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The dataset generation failed
Error code: DatasetGenerationError
Exception: CastError
Message: Couldn't cast
data: struct<paragraphText: string, label: string, headingText: string, documentId: string, title: string, (... 374 chars omitted)
child 0, paragraphText: string
child 1, label: string
child 2, headingText: string
child 3, documentId: string
child 4, title: string
child 5, assignees: list<item: string>
child 0, item: string
child 6, authors: list<item: string>
child 0, item: string
child 7, source: string
child 8, smiles: string
child 9, ipcCodes: list<item: string>
child 0, item: string
child 10, date: string
child 11, namerxndef: string
child 12, namerxn: string
child 13, diseases: list<item: string>
child 0, item: string
child 14, targets: list<item: string>
child 0, item: string
child 15, location: int64
child 16, rinchi: string
child 17, qualityRank: string
child 18, qualityFlags: list<item: struct<rank: string, description: string>>
child 0, item: struct<rank: string, description: string>
child 0, rank: string
child 1, description: string
child 19, stepLabel: string
components: list<item: struct<role: string, name: string, smiles: string, id: int64, orgName: string, stoichiome (... 461 chars omitted)
child 0, item: struct<role: string, name: string, smiles: string, id: int64, orgName: string, stoichiometry: int64, (... 449 chars omitted)
child 0, role: string
child 1, name: string
child 2, smiles: string
child 3, id: int64
child 4, orgName: str
...
: string, name: string, smiles: st (... 188 chars omitted)
child 0, item: struct<role: string, components: list<item: struct<role: string, name: string, smiles: string, quant (... 176 chars omitted)
child 0, role: string
child 1, components: list<item: struct<role: string, name: string, smiles: string, quantities: list<item: struct<type: st (... 37 chars omitted)
child 0, item: struct<role: string, name: string, smiles: string, quantities: list<item: struct<type: string, value (... 25 chars omitted)
child 0, role: string
child 1, name: string
child 2, smiles: string
child 3, quantities: list<item: struct<type: string, value: double, text: string>>
child 0, item: struct<type: string, value: double, text: string>
child 0, type: string
child 1, value: double
child 2, text: string
child 2, name: string
child 3, smiles: string
child 4, quantities: list<item: struct<value: double, text: string, type: string>>
child 0, item: struct<value: double, text: string, type: string>
child 0, value: double
child 1, text: string
child 2, type: string
positive: null
negative: null
yield: double
original_index: int64
to
{'original_index': Value('int64'), 'positive': Json(decode=True), 'negative': List(Json(decode=True)), 'yield': Value('float64')}
because column names don't match
Traceback: Traceback (most recent call last):
File "/usr/local/lib/python3.14/site-packages/datasets/builder.py", line 1827, in _prepare_split_single
for key, table in generator:
^^^^^^^^^
File "/src/services/worker/src/worker/job_runners/config/parquet_and_info.py", line 613, in wrapped
for item in generator(*args, **kwargs):
~~~~~~~~~^^^^^^^^^^^^^^^^^
File "/usr/local/lib/python3.14/site-packages/datasets/packaged_modules/json/json.py", line 343, in _generate_tables
self._cast_table(pa_table, json_field_paths=json_field_paths),
~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "/usr/local/lib/python3.14/site-packages/datasets/packaged_modules/json/json.py", line 132, in _cast_table
pa_table = table_cast(pa_table, self.info.features.arrow_schema)
File "/usr/local/lib/python3.14/site-packages/datasets/table.py", line 2378, in table_cast
return cast_table_to_schema(table, schema)
File "/usr/local/lib/python3.14/site-packages/datasets/table.py", line 2306, in cast_table_to_schema
raise CastError(
...<3 lines>...
)
datasets.table.CastError: Couldn't cast
data: struct<paragraphText: string, label: string, headingText: string, documentId: string, title: string, (... 374 chars omitted)
child 0, paragraphText: string
child 1, label: string
child 2, headingText: string
child 3, documentId: string
child 4, title: string
child 5, assignees: list<item: string>
child 0, item: string
child 6, authors: list<item: string>
child 0, item: string
child 7, source: string
child 8, smiles: string
child 9, ipcCodes: list<item: string>
child 0, item: string
child 10, date: string
child 11, namerxndef: string
child 12, namerxn: string
child 13, diseases: list<item: string>
child 0, item: string
child 14, targets: list<item: string>
child 0, item: string
child 15, location: int64
child 16, rinchi: string
child 17, qualityRank: string
child 18, qualityFlags: list<item: struct<rank: string, description: string>>
child 0, item: struct<rank: string, description: string>
child 0, rank: string
child 1, description: string
child 19, stepLabel: string
components: list<item: struct<role: string, name: string, smiles: string, id: int64, orgName: string, stoichiome (... 461 chars omitted)
child 0, item: struct<role: string, name: string, smiles: string, id: int64, orgName: string, stoichiometry: int64, (... 449 chars omitted)
child 0, role: string
child 1, name: string
child 2, smiles: string
child 3, id: int64
child 4, orgName: str
...
: string, name: string, smiles: st (... 188 chars omitted)
child 0, item: struct<role: string, components: list<item: struct<role: string, name: string, smiles: string, quant (... 176 chars omitted)
child 0, role: string
child 1, components: list<item: struct<role: string, name: string, smiles: string, quantities: list<item: struct<type: st (... 37 chars omitted)
child 0, item: struct<role: string, name: string, smiles: string, quantities: list<item: struct<type: string, value (... 25 chars omitted)
child 0, role: string
child 1, name: string
child 2, smiles: string
child 3, quantities: list<item: struct<type: string, value: double, text: string>>
child 0, item: struct<type: string, value: double, text: string>
child 0, type: string
child 1, value: double
child 2, text: string
child 2, name: string
child 3, smiles: string
child 4, quantities: list<item: struct<value: double, text: string, type: string>>
child 0, item: struct<value: double, text: string, type: string>
child 0, value: double
child 1, text: string
child 2, type: string
positive: null
negative: null
yield: double
original_index: int64
to
{'original_index': Value('int64'), 'positive': Json(decode=True), 'negative': List(Json(decode=True)), 'yield': Value('float64')}
because column names don't match
The above exception was the direct cause of the following exception:
Traceback (most recent call last):
File "/src/services/worker/src/worker/job_runners/config/parquet_and_info.py", line 1369, in compute_config_parquet_and_info_response
parquet_operations, partial, estimated_dataset_info = stream_convert_to_parquet(
~~~~~~~~~~~~~~~~~~~~~~~~~^
builder, max_dataset_size_bytes=max_dataset_size_bytes
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
)
^
File "/src/services/worker/src/worker/job_runners/config/parquet_and_info.py", line 948, in stream_convert_to_parquet
builder._prepare_split(split_generator=splits_generators[split], file_format="parquet")
~~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "/usr/local/lib/python3.14/site-packages/datasets/builder.py", line 1694, in _prepare_split
for job_id, done, content in self._prepare_split_single(
~~~~~~~~~~~~~~~~~~~~~~~~~~^
gen_kwargs=gen_kwargs, job_id=job_id, **_prepare_split_args
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
):
^
File "/usr/local/lib/python3.14/site-packages/datasets/builder.py", line 1880, in _prepare_split_single
raise DatasetGenerationError("An error occurred while generating the dataset") from e
datasets.exceptions.DatasetGenerationError: An error occurred while generating the datasetNeed help to make the dataset viewer work? Make sure to review how to configure the dataset viewer, and open a discussion for direct support.
original_index int64 | positive unknown | negative list | yield float64 |
|---|---|---|---|
64,630 | {
"Reactant": [
{
"iupac": "3,5-dichloro-4-methyl-pyridine-2-carbonitrile",
"smiles": "Cc1c(Cl)cnc(C#N)c1Cl"
},
{
"iupac": "quinolin-6-ylboronic acid",
"smiles": "OB(O)c1ccc2ncccc2c1"
}
],
"Product": [
{
"iupac": "3-chloro-4-methyl-5-quinolin-6-ylpyridine-2-carbon... | [
{
"Reactant": [
{
"iupac": "3,5-dichloro-4-methyl-pyridine-2-carbonitrile",
"smiles": "Cc1c(Cl)cnc(C#N)c1Cl"
},
{
"iupac": "quinolin-6-ylboronic acid",
"smiles": "OB(O)c1ccc2ncccc2c1"
}
],
"Product": [
{
"iupac": "3-chloro-4-methyl-5-... | null |
79,864 | {
"Reactant": [
{
"iupac": "Tert-butyl (2R,4aR)-10-chloro-11-fluoro-8-(2-isopropyl-4-methylpyridin-3-yl)-2,6-dimethyl-5,7-dioxo-1,2,4,4a,5,6,7,8-octahydro-3H-pyrazino[1′,2′:4,5]pyrazino[2,3-c][1,8]naphth yridine-3-carboxylate",
"smiles": "CC(C)c1nccc(C)c1N2C(=O)C3=C(N4C[C@@H](C)N(C[C@@H]4C(=O)N3C)C(=O... | [
{
"Reactant": [
{
"iupac": "Tert-butyl (2R,4aR)-10-chloro-11-fluoro-8-(2-isopropyl-4-methylpyridin-3-yl)-2,6-dimethyl-5,7-dioxo-1,2,4,4a,5,6,7,8-octahydro-3H-pyrazino[1′,2′:4,5]pyrazino[2,3-c][1,8]naphth yridine-3-carboxylate",
"smiles": "CC(C)c1nccc(C)c1N2C(=O)C3=C(N4C[C@@H](C)N(C[C@@H]4C... | 82.78 |
69,071 | {
"Reactant": [
{
"iupac": "4,7-dichloroquinazoline",
"smiles": "Clc1ccc2c(Cl)ncnc2c1"
},
{
"iupac": "4,4,5,5-tetramethyl-2-(3,4,5-trimethylphenyl)-1,3,2-dioxaborolane",
"smiles": "Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1C"
}
],
"Product": [
{
"iupac": "7-chloro-4-(3,4,5... | [
{
"Reactant": [
{
"iupac": "4,7-dichloroquinazoline",
"smiles": "Clc1ccc2c(Cl)ncnc2c1"
},
{
"iupac": "4,4,5,5-tetramethyl-2-(3,4,5-trimethylphenyl)-1,3,2-dioxaborolane",
"smiles": "Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(C)c1C"
}
],
"Product": [
{
... | null |
97,566 | {
"Reactant": [
{
"iupac": "(6-ethoxy-1-benzothiophen-2-yl)boronic acid",
"smiles": "C12=C(C=C(C=C1)OCC)SC(=C2)B(O)O"
}
],
"Product": [
{
"iupac": "2-[4-[difluoro-(3,4,5-trifluorophenoxy)methyl]-3,5-difluorophenyl]-6-ethoxy-1-benzothiophene",
"smiles": "C=1C(=C(C(=CC1C2=CC3=C(C... | [
{
"Reactant": [
{
"iupac": "(6-ethoxy-1-benzothiophen-2-yl)boronic acid",
"smiles": "C12=C(C=C(C=C1)OCC)SC(=C2)B(O)O"
}
],
"Product": [
{
"iupac": "2-[4-[difluoro-(3,4,5-trifluorophenoxy)methyl]-3,5-difluorophenyl]-6-ethoxy-1-benzothiophene",
"smiles": "... | null |
125,210 | {
"Reactant": [
{
"iupac": "N-[5-bromo-4-(2-hydroxyethyl)-2-pyridinyl]-2,2-dimethylpropanamide",
"smiles": "BrC=1C(=CC(=NC1)NC(C(C)(C)C)=O)CCO"
},
{
"iupac": "tert-butyl acetate;chlorozinc(1+)",
"smiles": "Cl[Zn]CC(OC(C)(C)C)=O"
}
],
"Product": [
{
"iupac": "tert-... | [
{
"Reactant": [
{
"iupac": "N-[5-bromo-4-(2-hydroxyethyl)-2-pyridinyl]-2,2-dimethylpropanamide",
"smiles": "BrC=1C(=CC(=NC1)NC(C(C)(C)C)=O)CCO"
},
{
"iupac": "tert-butyl acetate;chlorozinc(1+)",
"smiles": "Cl[Zn]CC(OC(C)(C)C)=O"
}
],
"Product": [
... | null |
13,916 | {
"Reactant": [
{
"iupac": "3-(5-(((tert-Butyldimethylsilyl)oxy)methyl)-2-(cyclopentylthio)-4- iodo-1H-imidazol-1-yl)pyridine",
"smiles": "CC(C)(C)[Si](C)(C)OCc1c(I)nc(SC2CCCC2)n1-c1cccnc1"
},
{
"iupac": "2-prop-2-ynoxyoxane",
"smiles": "C#CCOC1CCCCO1"
}
],
"Product": [
... | [
{
"Reactant": [
{
"iupac": "3-(5-(((tert-Butyldimethylsilyl)oxy)methyl)-2-(cyclopentylthio)-4- iodo-1H-imidazol-1-yl)pyridine",
"smiles": "CC(C)(C)[Si](C)(C)OCc1c(I)nc(SC2CCCC2)n1-c1cccnc1"
},
{
"iupac": "2-prop-2-ynoxyoxane",
"smiles": "C#CCOC1CCCCO1"
}
... | null |
43,965 | {
"Reactant": [
{
"iupac": "5-bromo-2-chloropyrimidine",
"smiles": "Clc1ncc(Br)cn1"
},
{
"iupac": "2-fluorophenylboronic acid",
"smiles": "OB(O)c1ccccc1F"
}
],
"Product": [
{
"iupac": "5-Bromo-2-(2-fluorophenyl)pyrimidine",
"smiles": "Fc1ccccc1-c1ncc(Br)cn1"... | [
{
"Reactant": [
{
"iupac": "5-bromo-2-chloropyrimidine",
"smiles": "Clc1ncc(Br)cn1"
},
{
"iupac": "2-fluorophenylboronic acid",
"smiles": "OB(O)c1ccccc1F"
}
],
"Product": [
{
"iupac": "5-Bromo-2-(2-fluorophenyl)pyrimidine",
"s... | 56 |
61,251 | {
"Reactant": [
{
"iupac": "1-[1-(4-fluorobenzyl)-4-iodo-1H-pyrrol-2-yl]ethanone",
"smiles": "CC(=O)c1cc(I)cn1Cc1ccc(F)cc1"
},
{
"iupac": "phenylboronic acid",
"smiles": "OB(O)c1ccccc1"
}
],
"Product": [
{
"iupac": "1-[1-(4-fluorobenzyl)-4-phenyl-1H-pyrrol-2-yl]et... | [
{
"Reactant": [
{
"iupac": "1-[1-(4-fluorobenzyl)-4-iodo-1H-pyrrol-2-yl]ethanone",
"smiles": "CC(=O)c1cc(I)cn1Cc1ccc(F)cc1"
},
{
"iupac": "phenylboronic acid",
"smiles": "OB(O)c1ccccc1"
}
],
"Product": [
{
"iupac": "1-[1-(4-fluorobenz... | null |
71,924 | {
"Reactant": [
{
"iupac": "2-chloro-4-phenyl-[1]benzothiolo[3,2-d]pyrimidine",
"smiles": "C1(=NC(=C2C(=N1)C3=C(S2)C=CC=C3)C4=CC=CC=C4)Cl"
}
],
"Product": [
{
"iupac": "4-phenyl-2-(3-triphenylen-2-ylphenyl)-[1]benzothiolo[3,2-d]pyrimidine",
"smiles": "C1=CC(=CC=C1)C2=C3C(=NC(=N... | [
{
"Reactant": [
{
"iupac": "2-chloro-4-phenyl-[1]benzothiolo[3,2-d]pyrimidine",
"smiles": "C1(=NC(=C2C(=N1)C3=C(S2)C=CC=C3)C4=CC=CC=C4)Cl"
}
],
"Product": [
{
"iupac": "4-phenyl-2-(3-triphenylen-2-ylphenyl)-[1]benzothiolo[3,2-d]pyrimidine",
"smiles": "C1... | null |
115,558 | {
"Reactant": [
{
"iupac": "5-Bromo-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methyl-N-((1-methyl-3- oxo-2,3, 5, 6,7, 8-hexahydroisoquinolin-4-yl)methyl)benzamide",
"smiles": "CCN(c1cc(Br)cc(C(=O)NCc2c3c(c(C)[nH]c2=O)CCCC3)c1C)C1CCOCC1"
},
{
"iupac": "(4-morpholinophenyl)boronic acid",
... | [
{
"Reactant": [
{
"iupac": "5-Bromo-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methyl-N-((1-methyl-3- oxo-2,3, 5, 6,7, 8-hexahydroisoquinolin-4-yl)methyl)benzamide",
"smiles": "CCN(c1cc(Br)cc(C(=O)NCc2c3c(c(C)[nH]c2=O)CCCC3)c1C)C1CCOCC1"
},
{
"iupac": "(4-morpholinophen... | null |
56,779 | {
"Reactant": [
{
"iupac": "2,4-diamino-5-iodo-6-methylpyrimidine",
"smiles": "Cc1nc(N)nc(N)c1I"
},
{
"iupac": "3-methyl-3-(4-trifluoromethylphenyl)-1-butyne",
"smiles": "C#CC(C)(C)c1ccc(C(F)(F)F)cc1"
}
],
"Product": [
{
"iupac": "2,4-diamino-6-methyl-5-[3-(4-trif... | [
{
"Reactant": [
{
"iupac": "2,4-diamino-5-iodo-6-methylpyrimidine",
"smiles": "Cc1nc(N)nc(N)c1I"
},
{
"iupac": "3-methyl-3-(4-trifluoromethylphenyl)-1-butyne",
"smiles": "C#CC(C)(C)c1ccc(C(F)(F)F)cc1"
}
],
"Product": [
{
"iupac": "2,4... | 96 |
59,592 | {
"Reactant": [
{
"iupac": "N-[5-bromo-3-(difluoromethoxy)pyrazin-2-yl]acetamide",
"smiles": "CC(=O)Nc1ncc(Br)nc1OC(F)F"
},
{
"iupac": "tert-butyl 7-cyano-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate",
"smiles": "CC(C)(C)OC(=O)n1cc(B2OC(C)(C)C(C)(C)O2)c2cccc(... | [
{
"Reactant": [
{
"iupac": "N-[5-bromo-3-(difluoromethoxy)pyrazin-2-yl]acetamide",
"smiles": "CC(=O)Nc1ncc(Br)nc1OC(F)F"
},
{
"iupac": "tert-butyl 7-cyano-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate",
"smiles": "CC(C)(C)OC(=O)n1cc(B2OC(C)... | null |
60,059 | {
"Reactant": [
{
"iupac": "Chloropyrazine",
"smiles": "Clc1cnccn1"
},
{
"iupac": "phenylmagnesium bromide",
"smiles": "[Br][Mg][c]1ccccc1"
}
],
"Product": [
{
"iupac": "2-phenylpyrazine",
"smiles": "c1ccc(-c2cnccn2)cc1"
}
],
"Catalyst": [
{
... | [
{
"Reactant": [
{
"iupac": "Chloropyrazine",
"smiles": "Clc1cnccn1"
},
{
"iupac": "phenylmagnesium bromide",
"smiles": "[Br][Mg][c]1ccccc1"
}
],
"Product": [
{
"iupac": "2-phenylpyrazine",
"smiles": "c1ccc(-c2cnccn2)cc1"
... | 39 |
58,532 | {
"Reactant": [
{
"iupac": "N-[[4-bromo-2-(2-methoxyethoxy)phenyl]methyl]-5-(4-propan-2-ylpyrimidin-5-yl)spiro[2H-pyrrolo[3,2-b]pyridine-3,1'-cyclopentane]-1-carboxamide",
"smiles": "N1=CN=CC(=C1C(C)C)C2=CC=C3C(=N2)C4(CN3C(NCC5=CC=C(C=C5OCCOC)Br)=O)CCCC4"
},
{
"iupac": "zinc dicyanide",
... | [
{
"Reactant": [
{
"iupac": "N-[[4-bromo-2-(2-methoxyethoxy)phenyl]methyl]-5-(4-propan-2-ylpyrimidin-5-yl)spiro[2H-pyrrolo[3,2-b]pyridine-3,1'-cyclopentane]-1-carboxamide",
"smiles": "N1=CN=CC(=C1C(C)C)C2=CC=C3C(=N2)C4(CN3C(NCC5=CC=C(C=C5OCCOC)Br)=O)CCCC4"
},
{
"iupac": ... | 34 |
104,495 | {
"Reactant": [
{
"iupac": "2-Chloro-1,3-dinitrobenzene",
"smiles": "O=[N+]([O-])c1cccc([N+](=O)[O-])c1Cl"
},
{
"iupac": "ethynyl-tri(propan-2-yl)silane",
"smiles": "C#C[Si](C(C)C)(C(C)C)C(C)C"
}
],
"Product": [
{
"iupac": "((2,6-dinitrophenyl)ethynyl)triisopropyl... | [
{
"Reactant": [
{
"iupac": "2-Chloro-1,3-dinitrobenzene",
"smiles": "O=[N+]([O-])c1cccc([N+](=O)[O-])c1Cl"
},
{
"iupac": "ethynyl-tri(propan-2-yl)silane",
"smiles": "C#C[Si](C(C)C)(C(C)C)C(C)C"
}
],
"Product": [
{
"iupac": "((2,6-dini... | 36 |
136,062 | {
"Reactant": [
{
"iupac": "5-bromo-2-[1-(oxan-2-ylmethyl)triazol-4-yl]-3-propan-2-ylpyridine",
"smiles": "C1(=C(N=CC(=C1)Br)C=2N=NN(C2)CC3CCCCO3)C(C)C"
}
],
"Product": [
{
"iupac": "3-[6-[1-(oxan-2-ylmethyl)triazol-4-yl]-5-propan-2-yl-3-pyridinyl]prop-2-yn-1-ol",
"smiles": "C1... | [
{
"Reactant": [
{
"iupac": "5-bromo-2-[1-(oxan-2-ylmethyl)triazol-4-yl]-3-propan-2-ylpyridine",
"smiles": "C1(=C(N=CC(=C1)Br)C=2N=NN(C2)CC3CCCCO3)C(C)C"
}
],
"Product": [
{
"iupac": "3-[6-[1-(oxan-2-ylmethyl)triazol-4-yl]-5-propan-2-yl-3-pyridinyl]prop-2-yn-1-ol... | null |
117,198 | {
"Reactant": [
{
"iupac": "3-bromo-2-cyclopropyloxy-6-methylpyridine",
"smiles": "Cc1ccc(Br)c(OC2CC2)n1"
},
{
"iupac": "(3-fluorophenyl)boronic acid",
"smiles": "OB(O)c1cccc(F)c1"
}
],
"Product": [
{
"iupac": "3-bromo-2-cyclopropyloxy-6-methylpyridine",
"sm... | [
{
"Reactant": [
{
"iupac": "3-bromo-2-cyclopropyloxy-6-methylpyridine",
"smiles": "Cc1ccc(Br)c(OC2CC2)n1"
},
{
"iupac": "(3-fluorophenyl)boronic acid",
"smiles": "OB(O)c1cccc(F)c1"
}
],
"Product": [
{
"iupac": "3-bromo-2-cyclopropylox... | null |
77,129 | {
"Reactant": [
{
"iupac": "trimethyl-[2-[[7-pyrazol-l-yl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)indazol-l-yl]methoxy]ethyl]silane",
"smiles": "CC1(C)OB(c2ccc(-n3cccn3)c3c2cnn3COCC[Si](C)(C)C)OC1(C)C"
},
{
"iupac": "3-fluoro-6-iodo- pyridazine",
"smiles": "Fc1ccc(I)nn1"
... | [
{
"Reactant": [
{
"iupac": "trimethyl-[2-[[7-pyrazol-l-yl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)indazol-l-yl]methoxy]ethyl]silane",
"smiles": "CC1(C)OB(c2ccc(-n3cccn3)c3c2cnn3COCC[Si](C)(C)C)OC1(C)C"
},
{
"iupac": "3-fluoro-6-iodo- pyridazine",
"smiles... | 15 |
47,315 | {
"Reactant": [
{
"iupac": "benzyl bromide",
"smiles": "BrCc1ccccc1"
},
{
"iupac": "2,6-Dimethyl-3-iodo-4-(phenylmethoxy)pyridine",
"smiles": "Cc1cc(OCc2ccccc2)c(I)c(C)n1"
}
],
"Product": [
{
"iupac": "2,6-dimethyl-3-phenylmethyl-4-(phenylmethoxy)pyridine",
... | [
{
"Reactant": [
{
"iupac": "benzyl bromide",
"smiles": "BrCc1ccccc1"
},
{
"iupac": "2,6-Dimethyl-3-iodo-4-(phenylmethoxy)pyridine",
"smiles": "Cc1cc(OCc2ccccc2)c(I)c(C)n1"
}
],
"Product": [
{
"iupac": "2,6-dimethyl-3-phenylmethyl-4-(p... | 44 |
72,388 | {
"Reactant": [
{
"iupac": "zinc carbanide",
"smiles": "C[Zn]C"
}
],
"Product": [
{
"iupac": "6-methyl-1'-(4'-oxospiro[1,3-dihydroindene-2,5'-1,3-oxazole]-2'-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one",
"smiles": "CC1=CC2=C(C=C1)C1(CCN(CC1)C=1OC3(C(N1)=O)CC1=CC=CC=C1C3)OC2=O"... | [
{
"Reactant": [
{
"iupac": "zinc carbanide",
"smiles": "C[Zn]C"
}
],
"Product": [
{
"iupac": "6-methyl-1'-(4'-oxospiro[1,3-dihydroindene-2,5'-1,3-oxazole]-2'-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one",
"smiles": "CC1=CC2=C(C=C1)C1(CCN(CC1)C=1OC3(C(N1)... | 65 |
25,619 | {
"Reactant": [
{
"iupac": "4-(6-chloro-4-(phenylsulfonyl)pyridin-2-yl)morpholine",
"smiles": "O=S(=O)(c1ccccc1)c1cc(Cl)nc(N2CCOCC2)c1"
},
{
"iupac": "5-bromothiazol-2-amine",
"smiles": "Nc1ncc(Br)s1"
}
],
"Product": [
{
"iupac": "5-(6-morpholino-4-(phenylsulfonyl... | [
{
"Reactant": [
{
"iupac": "4-(6-chloro-4-(phenylsulfonyl)pyridin-2-yl)morpholine",
"smiles": "O=S(=O)(c1ccccc1)c1cc(Cl)nc(N2CCOCC2)c1"
},
{
"iupac": "5-bromothiazol-2-amine",
"smiles": "Nc1ncc(Br)s1"
}
],
"Product": [
{
"iupac": "5-(... | 9 |
5,323 | {
"Reactant": [
{
"iupac": "(5-chloro-2-fluorophenyl)boronic acid",
"smiles": "OB(O)c1cc(Cl)ccc1F"
},
{
"iupac": "1-bromo-2-methoxynaphthalene",
"smiles": "COc1ccc2ccccc2c1Br"
}
],
"Product": [
{
"iupac": "1-(5-chloro-2-fluorophenyl)-2-methoxynaphthalene",
"... | [
{
"Reactant": [
{
"iupac": "(5-chloro-2-fluorophenyl)boronic acid",
"smiles": "OB(O)c1cc(Cl)ccc1F"
},
{
"iupac": "1-bromo-2-methoxynaphthalene",
"smiles": "COc1ccc2ccccc2c1Br"
}
],
"Product": [
{
"iupac": "1-(5-chloro-2-fluorophenyl)-... | 83 |
16,699 | {
"Reactant": [
{
"iupac": "2,4,7,8-tetrachloroquinoline",
"smiles": "Clc1cc(Cl)c2ccc(Cl)c(Cl)c2n1"
},
{
"iupac": "4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole",
"smiles": "CC1(C)OB(c2cn[nH]c2)OC1(C)C"
}
],
"Product": [
{
"iupac": "4,7,8-trichloro-2... | [
{
"Reactant": [
{
"iupac": "2,4,7,8-tetrachloroquinoline",
"smiles": "Clc1cc(Cl)c2ccc(Cl)c(Cl)c2n1"
},
{
"iupac": "4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole",
"smiles": "CC1(C)OB(c2cn[nH]c2)OC1(C)C"
}
],
"Product": [
{
... | 73 |
51,715 | {
"Reactant": [
{
"iupac": "2-octylindan-5-boronic acid",
"smiles": "CCCCCCCCC1Cc2ccc(B(O)O)cc2C1"
},
{
"iupac": "4-(trans-4-pentylcyclohexy)phenyl bromide",
"smiles": "CCCCC[C@H]1CC[C@H](c2ccc(Br)cc2)CC1"
}
],
"Product": [
{
"iupac": "2-octyl-5-[4-(trans-4-pentyl... | [
{
"Reactant": [
{
"iupac": "2-octylindan-5-boronic acid",
"smiles": "CCCCCCCCC1Cc2ccc(B(O)O)cc2C1"
},
{
"iupac": "4-(trans-4-pentylcyclohexy)phenyl bromide",
"smiles": "CCCCC[C@H]1CC[C@H](c2ccc(Br)cc2)CC1"
}
],
"Product": [
{
"iupac":... | 51 |
112,770 | {
"Reactant": [
{
"iupac": "methyl (1'R,3R)-5-hydroxyspiro[1,2-dihydroindene-3,2'-cyclopropane]-1'-carboxylate",
"smiles": "C1(=CC=C2C(=C1)[C@@]3(CC2)[C@@](C3)(C(=O)OC)[H])O"
}
],
"Product": [
{
"iupac": "methyl (1'R,3R)-5-(4-bromophenoxy)spiro[1,2-dihydroindene-3,2'-cyclopropane]-1'... | [
{
"Reactant": [
{
"iupac": "methyl (1'R,3R)-5-hydroxyspiro[1,2-dihydroindene-3,2'-cyclopropane]-1'-carboxylate",
"smiles": "C1(=CC=C2C(=C1)[C@@]3(CC2)[C@@](C3)(C(=O)OC)[H])O"
}
],
"Product": [
{
"iupac": "methyl (1'R,3R)-5-(4-bromophenoxy)spiro[1,2-dihydroindene... | null |
65,779 | {
"Reactant": [
{
"iupac": "2-bromo-5-ethenyl-1-fluoro-3-methylbenzene",
"smiles": "BrC1=C(C=C(C=C1C)C=C)F"
},
{
"iupac": "4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane",
"smiles": "C(C)(C)OB1OC(C(O1)(C)C)(C)C"
}
],
"Product": [
{
"iupac": "2-[[5-(4-eth... | [
{
"Reactant": [
{
"iupac": "2-bromo-5-ethenyl-1-fluoro-3-methylbenzene",
"smiles": "BrC1=C(C=C(C=C1C)C=C)F"
},
{
"iupac": "4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane",
"smiles": "C(C)(C)OB1OC(C(O1)(C)C)(C)C"
}
],
"Product": [
{
... | null |
89,909 | {
"Reactant": [
{
"iupac": "methyl (1R,2R)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]cyclopentanecarboxylate",
"smiles": "COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1"
},
{
"iupac": "2-bromo-5-nitro-thiophene",
"smiles": "O=[N+]([O-])c1ccc(Br)s1"
}
... | [
{
"Reactant": [
{
"iupac": "methyl (1R,2R)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]cyclopentanecarboxylate",
"smiles": "COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1"
},
{
"iupac": "2-bromo-5-nitro-thiophene",
"smiles": "O=[N+]([O-]... | null |
116,382 | {
"Reactant": [
{
"iupac": "(S)-ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate",
"smiles": "CCOC(=O)[C@@H](OC(C)(C)C)c1c(C)nc2cc(nn2c1I)C(=O)OCC"
},
{
"iupac": "7-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-b... | [
{
"Reactant": [
{
"iupac": "(S)-ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate",
"smiles": "CCOC(=O)[C@@H](OC(C)(C)C)c1c(C)nc2cc(nn2c1I)C(=O)OCC"
},
{
"iupac": "7-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl... | null |
54,863 | {
"Reactant": [
{
"iupac": "9-(2-chloro-4-pyridinyl)carbazole",
"smiles": "C=12C=3C(N(C1C=CC=C2)C4=CC=NC(=C4)Cl)=CC=CC3"
},
{
"iupac": "(2,4-difluorophenyl)boronic acid",
"smiles": "C1=CC(=CC(=C1B(O)O)F)F"
}
],
"Product": [
{
"iupac": "9-[2-(2,4-difluorophenyl)-4-... | [
{
"Reactant": [
{
"iupac": "9-(2-chloro-4-pyridinyl)carbazole",
"smiles": "C=12C=3C(N(C1C=CC=C2)C4=CC=NC(=C4)Cl)=CC=CC3"
},
{
"iupac": "(2,4-difluorophenyl)boronic acid",
"smiles": "C1=CC(=CC(=C1B(O)O)F)F"
}
],
"Product": [
{
"iupac":... | null |
74,934 | {
"Reactant": [
{
"iupac": "6-(7-chlorofuro[3,2-b]pyridin-2-yl)-5-methoxy-N,N-dimethylpyridine-3-carboxamide",
"smiles": "C1=C(C(=NC=C1C(=O)N(C)C)C=2OC3=C(N=CC=C3Cl)C2)OC"
}
],
"Product": [
{
"iupac": "6-[7-[3-cyano-4-(oxan-4-yloxy)phenyl]furo[3,2-b]pyridin-2-yl]-5-methoxy-N,N-dimeth... | [
{
"Reactant": [
{
"iupac": "6-(7-chlorofuro[3,2-b]pyridin-2-yl)-5-methoxy-N,N-dimethylpyridine-3-carboxamide",
"smiles": "C1=C(C(=NC=C1C(=O)N(C)C)C=2OC3=C(N=CC=C3Cl)C2)OC"
}
],
"Product": [
{
"iupac": "6-[7-[3-cyano-4-(oxan-4-yloxy)phenyl]furo[3,2-b]pyridin-2-yl... | null |
129,089 | {
"Reactant": [
{
"iupac": "tert-butyl piperidin-4-ylcarbamate",
"smiles": "CC(C)(C)OC(=O)NC1CCNCC1"
},
{
"iupac": "(4-(2,6-bis(benzyloxy)pyridin-3-yl)phenyl)boronic acid",
"smiles": "OB(O)c1ccc(-c2ccc(OCc3ccccc3)nc2OCc2ccccc2)cc1"
}
],
"Product": [
{
"iupac": "te... | [
{
"Reactant": [
{
"iupac": "tert-butyl piperidin-4-ylcarbamate",
"smiles": "CC(C)(C)OC(=O)NC1CCNCC1"
},
{
"iupac": "(4-(2,6-bis(benzyloxy)pyridin-3-yl)phenyl)boronic acid",
"smiles": "OB(O)c1ccc(-c2ccc(OCc3ccccc3)nc2OCc2ccccc2)cc1"
}
],
"Product": ... | 35 |
55,927 | {
"Reactant": [
{
"iupac": "2-[5-[3-[4-(5-bromo-2-chlorophenoxy)piperidin-1-yl]-1,2-oxazol-5-yl]tetrazol-2-yl]acetic acid",
"smiles": "BrC=1C=CC(=C(OC2CCN(CC2)C2=NOC(=C2)C=2N=NN(N2)CC(=O)O)C1)Cl"
},
{
"iupac": "[4-(trifluoromethoxy)phenyl]boronic acid",
"smiles": "FC(OC1=CC=C(C=C1)... | [
{
"Reactant": [
{
"iupac": "2-[5-[3-[4-(5-bromo-2-chlorophenoxy)piperidin-1-yl]-1,2-oxazol-5-yl]tetrazol-2-yl]acetic acid",
"smiles": "BrC=1C=CC(=C(OC2CCN(CC2)C2=NOC(=C2)C=2N=NN(N2)CC(=O)O)C1)Cl"
},
{
"iupac": "[4-(trifluoromethoxy)phenyl]boronic acid",
"smiles"... | null |
52,462 | {
"Reactant": [
{
"iupac": "2-(3-bromophenyl)ethanol",
"smiles": "BrC=1C=C(C=CC1)CCO"
},
{
"iupac": "phenylboronic acid",
"smiles": "C1(=CC=CC=C1)B(O)O"
}
],
"Product": [
{
"iupac": "2-(3-phenylphenyl)ethanol",
"smiles": "OCCC=1C=C(C=CC1)C1=CC=CC=C1"
}
... | [
{
"Reactant": [
{
"iupac": "2-(3-bromophenyl)ethanol",
"smiles": "BrC=1C=C(C=CC1)CCO"
},
{
"iupac": "phenylboronic acid",
"smiles": "C1(=CC=CC=C1)B(O)O"
}
],
"Product": [
{
"iupac": "2-(3-phenylphenyl)ethanol",
"smiles": "OCCC... | 87 |
13,755 | {
"Reactant": [
{
"iupac": "2-ethynyl-1,3,5-trimethoxybenzene",
"smiles": "COC1=C(C(=CC(=C1)OC)OC)C#C"
},
{
"iupac": "4-bromo-2,6-difluorobenzonitrile",
"smiles": "BrC1=CC(=C(C(=C1)F)C#N)F"
}
],
"Product": [
{
"iupac": "2,6-difluoro-4-[2-(2,4,6-trimethoxyphenyl)et... | [
{
"Reactant": [
{
"iupac": "2-ethynyl-1,3,5-trimethoxybenzene",
"smiles": "COC1=C(C(=CC(=C1)OC)OC)C#C"
},
{
"iupac": "4-bromo-2,6-difluorobenzonitrile",
"smiles": "BrC1=CC(=C(C(=C1)F)C#N)F"
}
],
"Product": [
{
"iupac": "2,6-difluoro-4... | 45 |
10,946 | {
"Reactant": [
{
"iupac": "8-[2,5-dichloro-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-4-yl]-3-oxa-8-azabicyclo[3.2.1]octane",
"smiles": "ClC1=NC(=C(C(=N1)N1C2COCC1CC2)Cl)N2C1COCC2CC1"
},
{
"iupac": "4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline",
"smiles": "NC1=CC=C... | [
{
"Reactant": [
{
"iupac": "8-[2,5-dichloro-6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-4-yl]-3-oxa-8-azabicyclo[3.2.1]octane",
"smiles": "ClC1=NC(=C(C(=N1)N1C2COCC1CC2)Cl)N2C1COCC2CC1"
},
{
"iupac": "4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline",
... | 0.708 |
22,090 | {
"Reactant": [
{
"iupac": "4-bromo-2,6-dichloropyridine",
"smiles": "Clc1cc(Br)cc(Cl)n1"
},
{
"iupac": "4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline",
"smiles": "Cc1ccc(N)cc1B1OC(C)(C)C(C)(C)O1"
}
],
"Product": [
{
"iupac": "3-(2,6-dichloropyri... | [
{
"Reactant": [
{
"iupac": "4-bromo-2,6-dichloropyridine",
"smiles": "Clc1cc(Br)cc(Cl)n1"
},
{
"iupac": "4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline",
"smiles": "Cc1ccc(N)cc1B1OC(C)(C)C(C)(C)O1"
}
],
"Product": [
{
... | null |
95,357 | {
"Reactant": [
{
"iupac": "4-bromo-2-(1H-indol-4-yl)-1,3-thiazole",
"smiles": "BrC=1N=C(SC1)C1=C2C=CNC2=CC=C1"
},
{
"iupac": "[2-chloro-4-(piperidine-1-carbonyl)phenyl]boronic acid",
"smiles": "ClC1=C(C=CC(=C1)C(=O)N1CCCCC1)B(O)O"
}
],
"Product": [
{
"iupac": "[3... | [
{
"Reactant": [
{
"iupac": "4-bromo-2-(1H-indol-4-yl)-1,3-thiazole",
"smiles": "BrC=1N=C(SC1)C1=C2C=CNC2=CC=C1"
},
{
"iupac": "[2-chloro-4-(piperidine-1-carbonyl)phenyl]boronic acid",
"smiles": "ClC1=C(C=CC(=C1)C(=O)N1CCCCC1)B(O)O"
}
],
"Product": ... | 15 |
85,680 | {
"Reactant": [
{
"iupac": "5-bromo-1H-indazole",
"smiles": "Brc1ccc2[nH]ncc2c1"
},
{
"iupac": "trimethylsilylacetylene",
"smiles": "C#C[Si](C)(C)C"
}
],
"Product": [
{
"iupac": "5-[2-(trimethylsilyl)ethynyl]-1H-indazole",
"smiles": "C[Si](C)(C)C#Cc1ccc2[nH]... | [
{
"Reactant": [
{
"iupac": "5-bromo-1H-indazole",
"smiles": "Brc1ccc2[nH]ncc2c1"
},
{
"iupac": "trimethylsilylacetylene",
"smiles": "C#C[Si](C)(C)C"
}
],
"Product": [
{
"iupac": "5-[2-(trimethylsilyl)ethynyl]-1H-indazole",
"sm... | 68 |
12,987 | {
"Reactant": [
{
"iupac": "3-(4-bromofuran-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine",
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3cc(Br)co3)c3cccnc32)cc1"
},
{
"iupac": "(R)-3-hydroxy-1-methyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one",
"smiles": "CN1CC[C@@](... | [
{
"Reactant": [
{
"iupac": "3-(4-bromofuran-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine",
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3cc(Br)co3)c3cccnc32)cc1"
},
{
"iupac": "(R)-3-hydroxy-1-methyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one",
"s... | 65 |
86,610 | {
"Reactant": [
{
"iupac": "methyl 5-{N-[(6-amino-5-iodopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}pentanoate",
"smiles": "COC(=O)CCCC[S](C)(=O)=NC(=O)c1cnc(N)c(I)c1"
},
{
"iupac": "3-Ethynylaniline",
"smiles": "C(#C)C=1C=C(N)C=CC1"
}
],
"Product": [
{
"iupac": ... | [
{
"Reactant": [
{
"iupac": "methyl 5-{N-[(6-amino-5-iodopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}pentanoate",
"smiles": "COC(=O)CCCC[S](C)(=O)=NC(=O)c1cnc(N)c(I)c1"
},
{
"iupac": "3-Ethynylaniline",
"smiles": "C(#C)C=1C=C(N)C=CC1"
}
],
"Product... | 68 |
24,111 | {
"Reactant": [
{
"iupac": "methyl (5S)-5-[tert-butyl(dimethyl)silyl]oxyhept-6-ynoate",
"smiles": "C([C@H](CCCC(OC)=O)O[Si](C)(C)C(C)(C)C)#C[H]"
}
],
"Product": [
{
"iupac": "methyl (E,5S)-5-[tert-butyl(dimethyl)silyl]oxy-10-hydroxydec-8-en-6-ynoate",
"smiles": "OC/C=C/C#C[C@H]... | [
{
"Reactant": [
{
"iupac": "methyl (5S)-5-[tert-butyl(dimethyl)silyl]oxyhept-6-ynoate",
"smiles": "C([C@H](CCCC(OC)=O)O[Si](C)(C)C(C)(C)C)#C[H]"
}
],
"Product": [
{
"iupac": "methyl (E,5S)-5-[tert-butyl(dimethyl)silyl]oxy-10-hydroxydec-8-en-6-ynoate",
"s... | null |
93,108 | {
"Reactant": [
{
"iupac": "4-(3-bromo-1-methylpyrazol-5-yl)morpholine",
"smiles": "BrC1=NN(C(=C1)N1CCOCC1)C"
}
],
"Product": [
{
"iupac": "3-amino-5-(dicyclopropylmethyl)-7-(1-methyl-5-morpholin-4-ylpyrazol-3-yl)-1H-pyrazolo[4,5-c]pyridin-4-one",
"smiles": "N1(C(C2=C(C(=C1)C=3... | [
{
"Reactant": [
{
"iupac": "4-(3-bromo-1-methylpyrazol-5-yl)morpholine",
"smiles": "BrC1=NN(C(=C1)N1CCOCC1)C"
}
],
"Product": [
{
"iupac": "3-amino-5-(dicyclopropylmethyl)-7-(1-methyl-5-morpholin-4-ylpyrazol-3-yl)-1H-pyrazolo[4,5-c]pyridin-4-one",
"smile... | 97 |
76,883 | {
"Reactant": [
{
"iupac": "(S)-6-((5-(2,3-dichloropyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1- yl)amino)-2-methoxy-5-(trifluoromethyl)nicotinaldehyde",
"smiles": "COc1nc(N[C@H]2CCCc3c(-c4ccnc(Cl)c4Cl)cccc32)c(C(F)(F)F)cc1C=O"
},
{
"iupac": "2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxab... | [
{
"Reactant": [
{
"iupac": "(S)-6-((5-(2,3-dichloropyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1- yl)amino)-2-methoxy-5-(trifluoromethyl)nicotinaldehyde",
"smiles": "COc1nc(N[C@H]2CCCc3c(-c4ccnc(Cl)c4Cl)cccc32)c(C(F)(F)F)cc1C=O"
},
{
"iupac": "2-methoxy-4-(4,4,5,5-tetram... | null |
21,532 | {
"Reactant": [
{
"iupac": "2-bromo-5-(2-methylpyrimidin-4-yl)-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine",
"smiles": "Cc1nccc(N2CCCCc3nc(Br)ccc32)n1"
},
{
"iupac": "Zn(CN)2",
"smiles": "N#[C][Zn][C]#N"
}
],
"Product": [
{
"iupac": "5-(2-methylpyrimidin-4-yl)-6,7,... | [
{
"Reactant": [
{
"iupac": "2-bromo-5-(2-methylpyrimidin-4-yl)-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine",
"smiles": "Cc1nccc(N2CCCCc3nc(Br)ccc32)n1"
},
{
"iupac": "Zn(CN)2",
"smiles": "N#[C][Zn][C]#N"
}
],
"Product": [
{
"iupac": "5... | null |
78,879 | {
"Reactant": [
{
"iupac": "2-chloro-N-ethyl-5-nitro-pyridin-4-amine",
"smiles": "CCNc1cc(Cl)ncc1[N+](=O)[O-]"
},
{
"iupac": "cyclopropylboronic acid",
"smiles": "OB(O)C1CC1"
}
],
"Product": [
{
"iupac": "2-cyclopropyl-N-ethyl-5-nitro-pyridin-4-amine",
"smil... | [
{
"Reactant": [
{
"iupac": "2-chloro-N-ethyl-5-nitro-pyridin-4-amine",
"smiles": "CCNc1cc(Cl)ncc1[N+](=O)[O-]"
},
{
"iupac": "cyclopropylboronic acid",
"smiles": "OB(O)C1CC1"
}
],
"Product": [
{
"iupac": "2-cyclopropyl-N-ethyl-5-nitro... | 45 |
94,774 | {
"Reactant": [
{
"iupac": "2-chloro-1-methyl-4-(trifluoromethyl)-1H-imidazole",
"smiles": "Cn1cc(C(F)(F)F)nc1Cl"
},
{
"iupac": "(2-fluoro-4-formylphenyl)boronic acid",
"smiles": "O=Cc1ccc(B(O)O)c(F)c1"
}
],
"Product": [
{
"iupac": "3-Fluoro-4-(1-methyl-4-(trifluo... | [
{
"Reactant": [
{
"iupac": "2-chloro-1-methyl-4-(trifluoromethyl)-1H-imidazole",
"smiles": "Cn1cc(C(F)(F)F)nc1Cl"
},
{
"iupac": "(2-fluoro-4-formylphenyl)boronic acid",
"smiles": "O=Cc1ccc(B(O)O)c(F)c1"
}
],
"Product": [
{
"iupac": "3... | 95 |
30,397 | {
"Reactant": [
{
"iupac": "5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine",
"smiles": "Cn1nnc(-c2ccc(Br)cn2)n1"
},
{
"iupac": "potassium tert-butyl N-[2-(trifluoroboranuidyl)ethyl]carbamate",
"smiles": "CC(C)(C)OC(=O)NCC[B-](F)(F)F.[K+]"
}
],
"Product": [
{
"iupac... | [
{
"Reactant": [
{
"iupac": "5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine",
"smiles": "Cn1nnc(-c2ccc(Br)cn2)n1"
},
{
"iupac": "potassium tert-butyl N-[2-(trifluoroboranuidyl)ethyl]carbamate",
"smiles": "CC(C)(C)OC(=O)NCC[B-](F)(F)F.[K+]"
}
],
"Prod... | null |
107,707 | {
"Reactant": [
{
"iupac": "6-Bromo-8-fluoro-3-methylquinazolin-4(3H)-one",
"smiles": "Cn1cnc2c(F)cc(Br)cc2c1=O"
},
{
"iupac": "2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane",
"smiles": "CB1OB(C)OB(C)O1"
}
],
"Product": [
{
"iupac": "8-Fluoro-3,6-dimethylquinazoli... | [
{
"Reactant": [
{
"iupac": "6-Bromo-8-fluoro-3-methylquinazolin-4(3H)-one",
"smiles": "Cn1cnc2c(F)cc(Br)cc2c1=O"
},
{
"iupac": "2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane",
"smiles": "CB1OB(C)OB(C)O1"
}
],
"Product": [
{
"iupac": "... | null |
89,047 | {
"Reactant": [
{
"iupac": "2,4-dichloro-3-methyl-1,8-naphthyridine",
"smiles": "ClC1=NC2=NC=CC=C2C(=C1C)Cl"
},
{
"iupac": "(5-fluoro-3-pyridinyl)boronic acid",
"smiles": "FC=1C=C(C=NC1)B(O)O"
}
],
"Product": [
{
"iupac": "4-chloro-2-(5-fluoro-3-pyridinyl)-3-methy... | [
{
"Reactant": [
{
"iupac": "2,4-dichloro-3-methyl-1,8-naphthyridine",
"smiles": "ClC1=NC2=NC=CC=C2C(=C1C)Cl"
},
{
"iupac": "(5-fluoro-3-pyridinyl)boronic acid",
"smiles": "FC=1C=C(C=NC1)B(O)O"
}
],
"Product": [
{
"iupac": "4-chloro-2-... | null |
42,187 | {
"Reactant": [
{
"iupac": "1-(4-fluorophenyl)-3-iodo-5-methylpyrazole",
"smiles": "Cc1cc(I)nn1-c1ccc(F)cc1"
},
{
"iupac": "2-ethynylpyrazine",
"smiles": "C#Cc1cnccn1"
}
],
"Product": [
{
"iupac": "2-((1-(4-fluorophenyl)-5-methyl-1H-pyrazol-3-yl)ethynyl)pyrazine",... | [
{
"Reactant": [
{
"iupac": "1-(4-fluorophenyl)-3-iodo-5-methylpyrazole",
"smiles": "Cc1cc(I)nn1-c1ccc(F)cc1"
},
{
"iupac": "2-ethynylpyrazine",
"smiles": "C#Cc1cnccn1"
}
],
"Product": [
{
"iupac": "2-((1-(4-fluorophenyl)-5-methyl-1H-p... | 27 |
46,509 | {
"Reactant": [
{
"iupac": "methyl 2-bromobenzoate",
"smiles": "COC(=O)c1ccccc1Br"
},
{
"iupac": "1,1-Dimethylethyl 2-borono-4-methyl-1H-indole-1-carboxylate",
"smiles": "Cc1cccc2c1cc(B(O)O)n2C(=O)OC(C)(C)C"
}
],
"Product": [
{
"iupac": "1,1-Dimethylethyl 2-[2-(me... | [
{
"Reactant": [
{
"iupac": "methyl 2-bromobenzoate",
"smiles": "COC(=O)c1ccccc1Br"
},
{
"iupac": "1,1-Dimethylethyl 2-borono-4-methyl-1H-indole-1-carboxylate",
"smiles": "Cc1cccc2c1cc(B(O)O)n2C(=O)OC(C)(C)C"
}
],
"Product": [
{
"iupac... | null |
39,563 | {
"Reactant": [
{
"iupac": "2-(4-Bromo-[2,4′-bipyrimidin]-2′-yl)-5-methoxyisoindoline",
"smiles": "COc1ccc2c(c1)CN(c1nccc(-c3nccc(Br)n3)n1)C2"
},
{
"iupac": "6-ethynylisoquinolin-1-amine",
"smiles": "C#Cc1ccc2c(N)nccc2c1"
}
],
"Product": [
{
"iupac": "6-((2′-(5-me... | [
{
"Reactant": [
{
"iupac": "2-(4-Bromo-[2,4′-bipyrimidin]-2′-yl)-5-methoxyisoindoline",
"smiles": "COc1ccc2c(c1)CN(c1nccc(-c3nccc(Br)n3)n1)C2"
},
{
"iupac": "6-ethynylisoquinolin-1-amine",
"smiles": "C#Cc1ccc2c(N)nccc2c1"
}
],
"Product": [
{
... | 26 |
53,174 | {
"Reactant": [
{
"iupac": "(2S)-3-(5-bromobenzotriazol-1-yl)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide",
"smiles": "C1=C(C(=CC(=C1)NC(=O)[C@@](C)(O)CN2C3=C(N=N2)C=C(C=C3)Br)C(F)(F)F)C#N"
}
],
"Product": [
{
"iupac": "(2S)-N-[4-cyano-3-(trifluoromethyl)pheny... | [
{
"Reactant": [
{
"iupac": "(2S)-3-(5-bromobenzotriazol-1-yl)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide",
"smiles": "C1=C(C(=CC(=C1)NC(=O)[C@@](C)(O)CN2C3=C(N=N2)C=C(C=C3)Br)C(F)(F)F)C#N"
}
],
"Product": [
{
"iupac": "(2S)-N-[4-cyano-3-... | null |
17,481 | {
"Reactant": [
{
"iupac": "4-Vinyl-phenylboronic acid",
"smiles": "C=Cc1ccc(B(O)O)cc1"
},
{
"iupac": "2-bromopyridine",
"smiles": "Brc1ccccn1"
}
],
"Product": [
{
"iupac": "2-(4-vinyl-phenyl)pyridine",
"smiles": "C=Cc1ccc(-c2ccccn2)cc1"
}
],
"Cataly... | [
{
"Reactant": [
{
"iupac": "4-Vinyl-phenylboronic acid",
"smiles": "C=Cc1ccc(B(O)O)cc1"
},
{
"iupac": "2-bromopyridine",
"smiles": "Brc1ccccn1"
}
],
"Product": [
{
"iupac": "2-(4-vinyl-phenyl)pyridine",
"smiles": "C=Cc1ccc(-c2... | 90 |
7,632 | {
"Reactant": [
{
"iupac": "2-formyl-4-methoxyphenylboronic acid",
"smiles": "COc1ccc(B(O)O)c(C=O)c1"
},
{
"iupac": "3-methyl-lH-pyrazole",
"smiles": "Cc1cc[nH]n1"
}
],
"Product": [
{
"iupac": "5-methoxy-2-(3-methyl-pyrazol-l-yl)- benzaldehyde",
"smiles": "C... | [
{
"Reactant": [
{
"iupac": "2-formyl-4-methoxyphenylboronic acid",
"smiles": "COc1ccc(B(O)O)c(C=O)c1"
},
{
"iupac": "3-methyl-lH-pyrazole",
"smiles": "Cc1cc[nH]n1"
}
],
"Product": [
{
"iupac": "5-methoxy-2-(3-methyl-pyrazol-l-yl)- ben... | 3 |
69,689 | {
"Reactant": [
{
"iupac": "methyl 2-[(3-bromo-6- chloro-4-quinolyl)amino] -5 -methyl-benzoate",
"smiles": "COC(=O)c1cc(C)ccc1Nc1c(Br)cnc2ccc(Cl)cc12"
},
{
"iupac": "2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane",
"smiles": "CC1(C)OB(C2=CCOCC2)OC1(C)C"
... | [
{
"Reactant": [
{
"iupac": "methyl 2-[(3-bromo-6- chloro-4-quinolyl)amino] -5 -methyl-benzoate",
"smiles": "COC(=O)c1cc(C)ccc1Nc1c(Br)cnc2ccc(Cl)cc12"
},
{
"iupac": "2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane",
"smiles": "CC1(C)OB(C2=... | 45 |
56,245 | {
"Reactant": [
{
"iupac": "bromozinc(1+);cyclobutane",
"smiles": "Br[Zn]C1CCC1"
}
],
"Product": [
{
"iupac": "(2S,3R,4S,5S)-3-tert-butyl-4-[(5-cyclobutyl-2-methoxy-3-pyridinyl)methoxy]-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylic acid",
"smiles": "C(C)(C)(C)[C@@H]1... | [
{
"Reactant": [
{
"iupac": "bromozinc(1+);cyclobutane",
"smiles": "Br[Zn]C1CCC1"
}
],
"Product": [
{
"iupac": "(2S,3R,4S,5S)-3-tert-butyl-4-[(5-cyclobutyl-2-methoxy-3-pyridinyl)methoxy]-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylic acid",
"smi... | 43 |
60,020 | {
"Reactant": [
{
"iupac": "morpholin-4-yl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone",
"smiles": "O1CCN(CC1)C(=O)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C"
},
{
"iupac": "trans-methyl (1R,2R)-2-(3-bromopyrazolo[1,5-a]pyridin-2-yl)-5,5-difluorocyclohexane-1-carboxylate",
... | [
{
"Reactant": [
{
"iupac": "morpholin-4-yl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone",
"smiles": "O1CCN(CC1)C(=O)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C"
},
{
"iupac": "trans-methyl (1R,2R)-2-(3-bromopyrazolo[1,5-a]pyridin-2-yl)-5,5-difluorocyclohexane-1... | null |
129,620 | {
"Reactant": [
{
"iupac": "l-amino-4-chloro-N-cyclopropylisoquinoline-6-carboxamide",
"smiles": "Nc1ncc(Cl)c2cc(C(=O)NC3CC3)ccc12"
},
{
"iupac": "l-methyl-4-[4-(tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-lH-pyrazole",
"smiles": "Cn1cc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)cn1"
}
]... | [
{
"Reactant": [
{
"iupac": "l-amino-4-chloro-N-cyclopropylisoquinoline-6-carboxamide",
"smiles": "Nc1ncc(Cl)c2cc(C(=O)NC3CC3)ccc12"
},
{
"iupac": "l-methyl-4-[4-(tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-lH-pyrazole",
"smiles": "Cn1cc(-c2ccc(B3OC(C)(C)C(C)(C)O... | 23 |
100,973 | {
"Reactant": [
{
"iupac": "1-(3-Bromo-4-methoxy-benzyl)-1H-[1,2,4]triazole",
"smiles": "COc1ccc(Cn2cncn2)cc1Br"
},
{
"iupac": "3-cyanophenylboronic acid",
"smiles": "N#Cc1cccc(B(O)O)c1"
}
],
"Product": [
{
"iupac": "2′-Methoxy-5′-[1,2,4]triazol-1-ylmethyl-bipheny... | [
{
"Reactant": [
{
"iupac": "1-(3-Bromo-4-methoxy-benzyl)-1H-[1,2,4]triazole",
"smiles": "COc1ccc(Cn2cncn2)cc1Br"
},
{
"iupac": "3-cyanophenylboronic acid",
"smiles": "N#Cc1cccc(B(O)O)c1"
}
],
"Product": [
{
"iupac": "2′-Methoxy-5′-[1,... | 52 |
134,414 | {
"Reactant": [
{
"iupac": "4-bromo-2-methoxyphenol",
"smiles": "C1(=C(C=CC(=C1)Br)O)OC"
}
],
"Product": [
{
"iupac": "4-bromo-2-methoxy-1-phenoxybenzene",
"smiles": "C1(=C(C=CC(=C1)Br)OC2=CC=CC=C2)OC"
}
],
"Catalyst": [
{
"iupac": "copper diacetate",
"s... | [
{
"Reactant": [
{
"iupac": "4-bromo-2-methoxyphenol",
"smiles": "C1(=C(C=CC(=C1)Br)O)OC"
}
],
"Product": [
{
"iupac": "4-bromo-2-methoxy-1-phenoxybenzene",
"smiles": "C1(=C(C=CC(=C1)Br)OC2=CC=CC=C2)OC"
}
],
"Catalyst": [
{
"sm... | null |
56,189 | {
"Reactant": [
{
"iupac": "1-(3-bromo-4-fluorophenyl)-2-[4-(difluoromethoxy)phenyl-]ethane-1,2-dione",
"smiles": "O=C(C(=O)c1ccc(F)c(Br)c1)c1ccc(OC(F)F)cc1"
},
{
"iupac": "ethynylcyclopropane",
"smiles": "C#CC1CC1"
}
],
"Product": [
{
"iupac": "1-[3-(cyclopropyle... | [
{
"Reactant": [
{
"iupac": "1-(3-bromo-4-fluorophenyl)-2-[4-(difluoromethoxy)phenyl-]ethane-1,2-dione",
"smiles": "O=C(C(=O)c1ccc(F)c(Br)c1)c1ccc(OC(F)F)cc1"
},
{
"iupac": "ethynylcyclopropane",
"smiles": "C#CC1CC1"
}
],
"Product": [
{
... | 68 |
80,598 | {
"Reactant": [
{
"iupac": "3-(4-bromophenyl)-1-methylpyrazole",
"smiles": "BrC1=CC=C(C=C1)C1=NN(C=C1)C"
},
{
"iupac": "5-(4-bromophenyl)-1-methylpyrazole",
"smiles": "BrC1=CC=C(C=C1)C1=CC=NN1C"
},
{
"iupac": "trimethyl-[2-(6-methyl-2-pyridinyl)ethynyl]silane",
... | [
{
"Reactant": [
{
"iupac": "3-(4-bromophenyl)-1-methylpyrazole",
"smiles": "BrC1=CC=C(C=C1)C1=NN(C=C1)C"
},
{
"iupac": "5-(4-bromophenyl)-1-methylpyrazole",
"smiles": "BrC1=CC=C(C=C1)C1=CC=NN1C"
},
{
"iupac": "trimethyl-[2-(6-methyl-2-pyridin... | null |
120,268 | {
"Reactant": [
{
"iupac": "N-[(4S)-2-amino-3'-bromospiro[5,6-dihydro-1,3-oxazine-4,5'-chromeno[2,3-b]pyridine]-7'-yl]-5-chloropyridine-2-carboxamide",
"smiles": "C1(=CC=C2C(=C1)[C@]3(C4=C(O2)N=CC(=C4)Br)CCOC(=N3)N)NC(C5=CC=C(C=N5)Cl)=O"
}
],
"Product": [
{
"iupac": "N-[(4S)-2-amino-... | [
{
"Reactant": [
{
"iupac": "N-[(4S)-2-amino-3'-bromospiro[5,6-dihydro-1,3-oxazine-4,5'-chromeno[2,3-b]pyridine]-7'-yl]-5-chloropyridine-2-carboxamide",
"smiles": "C1(=CC=C2C(=C1)[C@]3(C4=C(O2)N=CC(=C4)Br)CCOC(=N3)N)NC(C5=CC=C(C=N5)Cl)=O"
}
],
"Product": [
{
"iup... | null |
80,572 | {
"Reactant": [
{
"iupac": "trans-(1S,2S)-2-[(4-bromophenyl)methoxy]cyclopentan-1-amine",
"smiles": "N[C@H]1CCC[C@@H]1OCC2=CC=C(C=C2)Br"
}
],
"Product": [
{
"iupac": "trans-(1S,2S)-2-[[4-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]phenyl]methoxy]cyclopentan-1-amine",
"smiles": "N... | [
{
"Reactant": [
{
"iupac": "trans-(1S,2S)-2-[(4-bromophenyl)methoxy]cyclopentan-1-amine",
"smiles": "N[C@H]1CCC[C@@H]1OCC2=CC=C(C=C2)Br"
}
],
"Product": [
{
"iupac": "trans-(1S,2S)-2-[[4-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]phenyl]methoxy]cyclopentan-1-amin... | null |
43,661 | {
"Reactant": [
{
"iupac": "m-bromoacetophenone",
"smiles": "CC(=O)c1cccc(Br)c1"
},
{
"iupac": "3,5-dichlorobenzeneboronic acid",
"smiles": "OB(O)c1cc(Cl)cc(Cl)c1"
}
],
"Product": [
{
"iupac": "1-(3′,5′-dichloro-biphenyl-3-yl)-ethanone",
"smiles": "CC(=O)c1c... | [
{
"Reactant": [
{
"iupac": "m-bromoacetophenone",
"smiles": "CC(=O)c1cccc(Br)c1"
},
{
"iupac": "3,5-dichlorobenzeneboronic acid",
"smiles": "OB(O)c1cc(Cl)cc(Cl)c1"
}
],
"Product": [
{
"iupac": "1-(3′,5′-dichloro-biphenyl-3-yl)-ethanon... | 55 |
26,345 | {
"Reactant": [
{
"iupac": "2-(4,6-dichloro-1,3,5-triazin-2-yl)-1,3-benzoxazole-5,6-dicarbonitrile",
"smiles": "N#Cc1cc2nc(-c3nc(Cl)nc(Cl)n3)oc2cc1C#N"
},
{
"iupac": "2-[4-cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzimidazol-2-ylidene]propanedinitrile",
"smiles": "CC1(... | [
{
"Reactant": [
{
"iupac": "2-(4,6-dichloro-1,3,5-triazin-2-yl)-1,3-benzoxazole-5,6-dicarbonitrile",
"smiles": "N#Cc1cc2nc(-c3nc(Cl)nc(Cl)n3)oc2cc1C#N"
},
{
"iupac": "2-[4-cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzimidazol-2-ylidene]propanedinitrile",
... | 70 |
24,485 | {
"Reactant": [
{
"iupac": "(4-amino-3-dimethylphosphorylphenyl) trifluoromethanesulfonate",
"smiles": "CP(C)(=O)c1cc(OS(=O)(=O)C(F)(F)F)ccc1N"
},
{
"iupac": "1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole",
"smiles": "Cn1ccc(B2OC(C)(C)C(C)(C)O2)n1"
}
],
"... | [
{
"Reactant": [
{
"iupac": "(4-amino-3-dimethylphosphorylphenyl) trifluoromethanesulfonate",
"smiles": "CP(C)(=O)c1cc(OS(=O)(=O)C(F)(F)F)ccc1N"
},
{
"iupac": "1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole",
"smiles": "Cn1ccc(B2OC(C)(C)C(C)(C)O... | null |
97,692 | {
"Reactant": [
{
"iupac": "6-(2-chloropyrimidin-5-yl)-2-methyl-3-[(1S,3S)-3-methyl-1,3-dihydro-2-benzofuran-1-yl]imidazo[1,2-a]pyridine",
"smiles": "ClC1=NC=C(C=N1)C=1C=CC=2N(C1)C(=C(N2)C)[C@H]2O[C@H](C1=C2C=CC=C1)C"
},
{
"iupac": "ethyl (1S,5S,6R)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboro... | [
{
"Reactant": [
{
"iupac": "6-(2-chloropyrimidin-5-yl)-2-methyl-3-[(1S,3S)-3-methyl-1,3-dihydro-2-benzofuran-1-yl]imidazo[1,2-a]pyridine",
"smiles": "ClC1=NC=C(C=N1)C=1C=CC=2N(C1)C(=C(N2)C)[C@H]2O[C@H](C1=C2C=CC=C1)C"
},
{
"iupac": "ethyl (1S,5S,6R)-3-(4,4,5,5-tetrameth... | 10.5 |
51,381 | {
"Reactant": [
{
"iupac": "Ethyl 3-bromo-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate",
"smiles": "CCOC(=O)c1sc2[nH]c(=O)ccc2c1Br"
},
{
"iupac": "4-tolylboronic acid",
"smiles": "Cc1ccc(B(O)O)cc1"
}
],
"Product": [
{
"iupac": "Ethyl 3-bromo-7-(4-methylphe... | [
{
"Reactant": [
{
"iupac": "Ethyl 3-bromo-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate",
"smiles": "CCOC(=O)c1sc2[nH]c(=O)ccc2c1Br"
},
{
"iupac": "4-tolylboronic acid",
"smiles": "Cc1ccc(B(O)O)cc1"
}
],
"Product": [
{
"iupac":... | 80 |
32,795 | {
"Reactant": [
{
"iupac": "4-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one",
"smiles": "CC(O)c1oc(=O)c2ccccc2c1Br"
},
{
"iupac": "2-[4-fluoro-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane",
"smiles": "CC1(C)OB(c2ccc(F)c(C3OC(C)(C)C(C)(C)O3... | [
{
"Reactant": [
{
"iupac": "4-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one",
"smiles": "CC(O)c1oc(=O)c2ccccc2c1Br"
},
{
"iupac": "2-[4-fluoro-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane",
"smiles": "CC1(C)OB(c2ccc(F)c... | 50 |
3,688 | {
"Reactant": [
{
"iupac": "trans-4-{[6-[(6-bromo-1 ,3-benzothiazol-2-yl)amino]-4-(1 H-pyrazol-1 -ylmethyl)- 2-pyridinyl]amino}cyclohexanol",
"smiles": "O[C@H]1CC[C@H](Nc2cc(Cn3cccn3)cc(Nc3nc4ccc(Br)cc4s3)n2)CC1"
},
{
"iupac": "1 ,1-dimethylethyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborola... | [
{
"Reactant": [
{
"iupac": "trans-4-{[6-[(6-bromo-1 ,3-benzothiazol-2-yl)amino]-4-(1 H-pyrazol-1 -ylmethyl)- 2-pyridinyl]amino}cyclohexanol",
"smiles": "O[C@H]1CC[C@H](Nc2cc(Cn3cccn3)cc(Nc3nc4ccc(Br)cc4s3)n2)CC1"
},
{
"iupac": "1 ,1-dimethylethyl 4-(4,4,5,5-tetramethyl-... | 13 |
122,770 | {
"Reactant": [
{
"iupac": "2-bromo-4-(3,5-dimethyl-1,2-oxazol-4-yl)-6-nitroaniline",
"smiles": "C1(=C(C=C(C=C1Br)C2=C(ON=C2C)C)[N+](=O)[O-])N"
}
],
"Product": [
{
"iupac": "4-(3,5-dimethyl-1,2-oxazol-4-yl)-2-nitro-6-(1,3,5-trimethylpyrazol-4-yl)aniline",
"smiles": "C1(=C(C=C(C... | [
{
"Reactant": [
{
"iupac": "2-bromo-4-(3,5-dimethyl-1,2-oxazol-4-yl)-6-nitroaniline",
"smiles": "C1(=C(C=C(C=C1Br)C2=C(ON=C2C)C)[N+](=O)[O-])N"
}
],
"Product": [
{
"iupac": "4-(3,5-dimethyl-1,2-oxazol-4-yl)-2-nitro-6-(1,3,5-trimethylpyrazol-4-yl)aniline",
... | 53 |
61,907 | {
"Reactant": [
{
"iupac": "2,2-dimethyl-4-oxo-7-fluoro-thiochroman-6-yl trifluoromethanesulfonate",
"smiles": "CC1(C)CC(=O)c2cc(OS(=O)(=O)C(F)(F)F)c(F)cc2S1"
},
{
"iupac": "trimethylsilylacetylene",
"smiles": "C#C[Si](C)(C)C"
}
],
"Product": [
{
"iupac": "2,2-Dim... | [
{
"Reactant": [
{
"iupac": "2,2-dimethyl-4-oxo-7-fluoro-thiochroman-6-yl trifluoromethanesulfonate",
"smiles": "CC1(C)CC(=O)c2cc(OS(=O)(=O)C(F)(F)F)c(F)cc2S1"
},
{
"iupac": "trimethylsilylacetylene",
"smiles": "C#C[Si](C)(C)C"
}
],
"Product": [
... | 78 |
31,187 | {
"Reactant": [
{
"iupac": "N-(5-(5-bromo-2-methoxyphenyl)isoxazol-3-yl)-N-(2,4-dimethoxybenzyl)-2,6-dimethoxybenzenesulfonamide",
"smiles": "COc1ccc(CN(c2cc(-c3cc(Br)ccc3OC)on2)S(=O)(=O)c2c(OC)cccc2OC)c(OC)c1"
},
{
"iupac": "(1H-pyrazol-5-yl)boronic acid",
"smiles": "OB(O)c1ccn[nH... | [
{
"Reactant": [
{
"iupac": "N-(5-(5-bromo-2-methoxyphenyl)isoxazol-3-yl)-N-(2,4-dimethoxybenzyl)-2,6-dimethoxybenzenesulfonamide",
"smiles": "COc1ccc(CN(c2cc(-c3cc(Br)ccc3OC)on2)S(=O)(=O)c2c(OC)cccc2OC)c(OC)c1"
},
{
"iupac": "(1H-pyrazol-5-yl)boronic acid",
"smi... | null |
1,883 | {
"Reactant": [
{
"iupac": "8-bromo-3-[(4-methoxyphenyl)methyl]-2-{[(4- methoxyphenyl)methyl]sulfanyl}-7-methylpyrazolo[1,5-a][1,3,5]triazin-4-one hydrobromide",
"smiles": "Br.COc1ccc(CSc2nc3c(Br)c(C)nn3c(=O)n2Cc2ccc(OC)cc2)cc1"
},
{
"iupac": "6-methylpyridin-3-ylboronic acid",
"sm... | [
{
"Reactant": [
{
"iupac": "8-bromo-3-[(4-methoxyphenyl)methyl]-2-{[(4- methoxyphenyl)methyl]sulfanyl}-7-methylpyrazolo[1,5-a][1,3,5]triazin-4-one hydrobromide",
"smiles": "Br.COc1ccc(CSc2nc3c(Br)c(C)nn3c(=O)n2Cc2ccc(OC)cc2)cc1"
},
{
"iupac": "6-methylpyridin-3-ylboroni... | null |
127,538 | {
"Reactant": [
{
"iupac": "ethyl 6-[2-[[(4-bromobenzoyl)-cyclopropylamino]methyl]phenoxy]hexanoate",
"smiles": "C1=CC=CC(=C1OCCCCCC(OCC)=O)CN(C(C2=CC=C(C=C2)Br)=O)C3CC3"
}
],
"Product": [
{
"iupac": "ethyl 6-[2-[[cyclopropyl-[4-(furan-2-yl)benzoyl]amino]methyl]phenoxy]hexanoate",
... | [
{
"Reactant": [
{
"iupac": "ethyl 6-[2-[[(4-bromobenzoyl)-cyclopropylamino]methyl]phenoxy]hexanoate",
"smiles": "C1=CC=CC(=C1OCCCCCC(OCC)=O)CN(C(C2=CC=C(C=C2)Br)=O)C3CC3"
}
],
"Product": [
{
"iupac": "ethyl 6-[2-[[cyclopropyl-[4-(furan-2-yl)benzoyl]amino]methyl]... | null |
25,946 | {
"Reactant": [
{
"iupac": "3-bromo-6-(2-furyl)-5-pyrimidin-4-ylpyridin-2-amine",
"smiles": "Nc1nc(-c2ccco2)c(-c2ccncn2)cc1Br"
},
{
"iupac": "trimethylsilylacetylene",
"smiles": "C#C[Si](C)(C)C"
}
],
"Product": [
{
"iupac": "6-furan-2-yl-5-pyrimidin-4-yl-3- trimet... | [
{
"Reactant": [
{
"iupac": "3-bromo-6-(2-furyl)-5-pyrimidin-4-ylpyridin-2-amine",
"smiles": "Nc1nc(-c2ccco2)c(-c2ccncn2)cc1Br"
},
{
"iupac": "trimethylsilylacetylene",
"smiles": "C#C[Si](C)(C)C"
}
],
"Product": [
{
"iupac": "6-furan-2... | 47 |
268 | {
"Reactant": [
{
"iupac": "methyl 2-bromo-4-cyanobenzoate",
"smiles": "COC(=O)c1ccc(C#N)cc1Br"
},
{
"iupac": "methyl 2-bromo-4-cyanobenzoate",
"smiles": "COC(=O)c1ccc(C#N)cc1Br"
},
{
"iupac": "2,6-dichloropyridin-4-ylboronic acid",
"smiles": "OB(O)c1cc(Cl)nc(Cl... | [
{
"Reactant": [
{
"iupac": "methyl 2-bromo-4-cyanobenzoate",
"smiles": "COC(=O)c1ccc(C#N)cc1Br"
},
{
"iupac": "methyl 2-bromo-4-cyanobenzoate",
"smiles": "COC(=O)c1ccc(C#N)cc1Br"
},
{
"iupac": "2,6-dichloropyridin-4-ylboronic acid",
"... | null |
128,283 | {
"Reactant": [
{
"iupac": "3-[(S)-{3-[(1S)-1-(3-bromo-5-fluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl}(4-chlorophenyl)methyl]benzonitrile",
"smiles": "CC(C)(F)[C@H](c1cc(F)cc(Br)c1)C1CN([C@@H](c2ccc(Cl)cc2)c2cccc(C#N)c2)C1"
},
{
"iupac": "Zn(CN)2",
"smiles": "N#[C][Zn][C]#N"... | [
{
"Reactant": [
{
"iupac": "3-[(S)-{3-[(1S)-1-(3-bromo-5-fluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl}(4-chlorophenyl)methyl]benzonitrile",
"smiles": "CC(C)(F)[C@H](c1cc(F)cc(Br)c1)C1CN([C@@H](c2ccc(Cl)cc2)c2cccc(C#N)c2)C1"
},
{
"iupac": "Zn(CN)2",
"smile... | null |
92,566 | {
"Reactant": [
{
"iupac": "1-(benzenesulfonyl)-4-(2,3-difluorophenyl)-2-iodopyrrolo[2,3-b]pyridine",
"smiles": "FC1=C(C=CC=C1F)C1=C2C(=NC=C1)N(C(=C2)I)S(=O)(=O)C2=CC=CC=C2"
},
{
"iupac": "tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate",
... | [
{
"Reactant": [
{
"iupac": "1-(benzenesulfonyl)-4-(2,3-difluorophenyl)-2-iodopyrrolo[2,3-b]pyridine",
"smiles": "FC1=C(C=CC=C1F)C1=C2C(=NC=C1)N(C(=C2)I)S(=O)(=O)C2=CC=CC=C2"
},
{
"iupac": "tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridin... | null |
117,224 | {
"Reactant": [
{
"iupac": "methyl 3-[(1-benzylindol-5-yl)amino]-6-chloropyridazine-4-carboxylate",
"smiles": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)NC=1N=NC(=CC1C(=O)OC)Cl"
},
{
"iupac": "cyclopropylboronic acid;hydrate",
"smiles": "O.C1(CC1)B(O)O"
}
],
"Product": [
{
... | [
{
"Reactant": [
{
"iupac": "methyl 3-[(1-benzylindol-5-yl)amino]-6-chloropyridazine-4-carboxylate",
"smiles": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)NC=1N=NC(=CC1C(=O)OC)Cl"
},
{
"iupac": "cyclopropylboronic acid;hydrate",
"smiles": "O.C1(CC1)B(O)O"
}
],
... | 55 |
56,307 | {
"Reactant": [
{
"iupac": "4-methoxybenzeneboronic acid",
"smiles": "COc1ccc(B(O)O)cc1"
},
{
"iupac": "3-bromobenzonitrile",
"smiles": "N#Cc1cccc(Br)c1"
}
],
"Product": [
{
"iupac": "3'-Cyano-4-methoxybiphenyl",
"smiles": "COc1ccc(-c2cccc(C#N)c2)cc1"
}
... | [
{
"Reactant": [
{
"iupac": "4-methoxybenzeneboronic acid",
"smiles": "COc1ccc(B(O)O)cc1"
},
{
"iupac": "3-bromobenzonitrile",
"smiles": "N#Cc1cccc(Br)c1"
}
],
"Product": [
{
"iupac": "3'-Cyano-4-methoxybiphenyl",
"smiles": "CO... | 97 |
102,213 | {
"Reactant": [
{
"iupac": "2,4-dichloropyridine",
"smiles": "Clc1ccnc(Cl)c1"
},
{
"iupac": "3-thiopheneboronic acid",
"smiles": "OB(O)c1ccsc1"
}
],
"Product": [
{
"iupac": "4-Chloro-2-thiophen-3-yl-Pyridine",
"smiles": "Clc1ccnc(-c2ccsc2)c1"
}
],
"C... | [
{
"Reactant": [
{
"iupac": "2,4-dichloropyridine",
"smiles": "Clc1ccnc(Cl)c1"
},
{
"iupac": "3-thiopheneboronic acid",
"smiles": "OB(O)c1ccsc1"
}
],
"Product": [
{
"iupac": "4-Chloro-2-thiophen-3-yl-Pyridine",
"smiles": "Clc1c... | null |
42,887 | {
"Reactant": [
{
"iupac": "4-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine",
"smiles": "C1(=CN=C2C(=C1Br)C=CN2[H])Cl"
}
],
"Product": [
{
"iupac": "N-[2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide",
"smiles": "C1(=CN=C2C(=C1C=3C(=CC=CC3)N(C(C)=O)[H])C=CN2[H])Cl"
}
... | [
{
"Reactant": [
{
"iupac": "4-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine",
"smiles": "C1(=CN=C2C(=C1Br)C=CN2[H])Cl"
}
],
"Product": [
{
"iupac": "N-[2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide",
"smiles": "C1(=CN=C2C(=C1C=3C(=CC=CC3)N(C(C)=O... | null |
92,469 | {
"Reactant": [
{
"iupac": "4-Bromophenyl-sulfonic acid-(4-hydroxybutyl)-amide",
"smiles": "O=S(=O)(NCCCCO)c1ccc(Br)cc1"
},
{
"iupac": "4-Trifluoromethylphenyl boronic acid",
"smiles": "OB(O)c1ccc(C(F)(F)F)cc1"
}
],
"Product": [
{
"iupac": "N-(4-hydroxybutyl)-4-[4... | [
{
"Reactant": [
{
"iupac": "4-Bromophenyl-sulfonic acid-(4-hydroxybutyl)-amide",
"smiles": "O=S(=O)(NCCCCO)c1ccc(Br)cc1"
},
{
"iupac": "4-Trifluoromethylphenyl boronic acid",
"smiles": "OB(O)c1ccc(C(F)(F)F)cc1"
}
],
"Product": [
{
"iu... | null |
116,157 | {
"Reactant": [
{
"iupac": "N-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)iminodiacetic acid diethyl ester",
"smiles": "CCOC(=O)CN(CC(=O)OCC)c1cc(Br)cc2CCOc12"
},
{
"iupac": "zinc cyanide",
"smiles": "[Zn++].[C-]#N.[C-]#N"
}
],
"Product": [
{
"iupac": "ethyl 2-[(5-cyan... | [
{
"Reactant": [
{
"iupac": "N-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)iminodiacetic acid diethyl ester",
"smiles": "CCOC(=O)CN(CC(=O)OCC)c1cc(Br)cc2CCOc12"
},
{
"iupac": "zinc cyanide",
"smiles": "[Zn++].[C-]#N.[C-]#N"
}
],
"Product": [
{
... | 37 |
75,672 | {
"Reactant": [
{
"iupac": "5-((6-bromopyridin-2-yl)oxy)-2-fluorophenol",
"smiles": "Oc1cc(Oc2cccc(Br)n2)ccc1F"
},
{
"iupac": "thiophen-2-ylboronic acid",
"smiles": "S1C(=CC=C1)B(O)O"
}
],
"Product": [
{
"iupac": "2-fluoro-5-((6-(thiophen-2-yl)pyridin-2-yl)oxy)phe... | [
{
"Reactant": [
{
"iupac": "5-((6-bromopyridin-2-yl)oxy)-2-fluorophenol",
"smiles": "Oc1cc(Oc2cccc(Br)n2)ccc1F"
},
{
"iupac": "thiophen-2-ylboronic acid",
"smiles": "S1C(=CC=C1)B(O)O"
}
],
"Product": [
{
"iupac": "2-fluoro-5-((6-(thio... | 98 |
33,230 | {
"Reactant": [
{
"iupac": "5-bromo-1-methyl-3-pentyl-2-phenyl-1H-indole",
"smiles": "CCCCCc1c(-c2ccccc2)n(C)c2ccc(Br)cc12"
},
{
"iupac": "4-methoxyphenylboronic acid",
"smiles": "COc1ccc(B(O)O)cc1"
}
],
"Product": [
{
"iupac": "5-(4-Methoxy-phenyl)-1-methyl-3-pen... | [
{
"Reactant": [
{
"iupac": "5-bromo-1-methyl-3-pentyl-2-phenyl-1H-indole",
"smiles": "CCCCCc1c(-c2ccccc2)n(C)c2ccc(Br)cc12"
},
{
"iupac": "4-methoxyphenylboronic acid",
"smiles": "COc1ccc(B(O)O)cc1"
}
],
"Product": [
{
"iupac": "5-(4-... | null |
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