dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e620bb8c96c044ae89795f40aff01e3e | CCOC(=O)c1c[nH]c(-c2ccccc2)c1>>OCc1c[nH]c(-c2ccccc2)c1 | O.[H-].C(C(C)C)[Al+]CC(C)C.C1(=CC=CC=C1)C1=CC(=CN1)C(=O)OCC>>C1(=CC=CC=C1)C1=CC(=CN1)CO | CCO[C:2](=[O:1])[c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13]1>>[OH:1][CH2:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13]1 | CCOC(=O)c1c[nH]c(-c2ccccc2)c1 | OCc1c[nH]c(-c2ccccc2)c1 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2ccc[nH]2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 87 | [{"value": 87.0, "product": "C1(=CC=CC=C1)C1=CC(=CN1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "C1(=CC=CC=C1)C1=CC(=CN1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | A solution (100 mL) of ethyl 5-phenyl-1H-pyrrole-3-carboxylate (2.16 g) in tetrahydrofuran was cooled to −78° C., and a 1.5 mol/L solution (24 mL) of diisobutylaluminum hydride in toluene was added dropwise over 10 min. The mixture was further stirred at −78° C. for 1 hr, water (2 mL) was added dropwise over 2 min, and... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cc[nH]c1.c1ccccc1 | HO- | O1CCCC1.C1(=CC=CC=C1)C | -78 | 1 | CCOC(=O)c1c[nH]c(-c2ccccc2)c1>O1CCCC1.C1(=CC=CC=C1)C>OCc1c[nH]c(-c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff64cf2715224e8988e69887cb80030a | OCc1c[nH]c(-c2ccccc2)c1>>O=Cc1c[nH]c(-c2ccccc2)c1 | C1(=CC=CC=C1)C1=CC(=CN1)CO.C[N+]1(CCOCC1)[O-]>>C1(=CC=CC=C1)C1=CC(=CN1)C=O | [OH:1][CH2:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13]1>>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13]1 | OCc1c[nH]c(-c2ccccc2)c1 | O=Cc1c[nH]c(-c2ccccc2)c1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | C(C)#N | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-c2ccc[nH]2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 62 | [{"value": 62.0, "product": "C1(=CC=CC=C1)C1=CC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "C1(=CC=CC=C1)C1=CC(=CN1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution (45 mL) of (5-phenyl-1H-pyrrol-3-yl)methanol (1.51 g) in acetonitrile were added tetra-n-propylammonium perruthenate (0.46 g), N-methylmorpholine N-oxide (2.36 g) and molecular sieves 4A powder (4.5 g), and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was filtered through c... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cc[nH]c1.c1ccccc1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(C)#N | null | 1.5 | OCc1c[nH]c(-c2ccccc2)c1>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(C)#N>O=Cc1c[nH]c(-c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-263eb300394041fc896f191d181331c3 | Cc1c(CO)c[nH]c1-c1ccccc1F>>Cc1c(C=O)c[nH]c1-c1ccccc1F | FC1=C(C=CC=C1)C1=C(C(=CN1)CO)C.C[N+]1(CCOCC1)[O-]>>FC1=C(C=CC=C1)C1=C(C(=CN1)C=O)C | [CH3:1][c:2]1[c:3]([CH2:4][OH:5])[cH:6][nH:7][c:8]1-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[F:15]>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][nH:7][c:8]1-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[F:15] | Cc1c(CO)c[nH]c1-c1ccccc1F | Cc1c(C=O)c[nH]c1-c1ccccc1F | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | null | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-c2ccc[nH]2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 58 | [{"value": 58.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 15 and using [5-(2-fluorophenyl)-4-methyl-1H-pyrrol-3-yl]methanol (1.17 g), tetra-n-propylammonium perruthenate (101 mg), N-methylmorpholine N-oxide (1.01 g) and molecular sieves 4A powder (572 mg), the title compound was obtained as pale-pink crystals (yield 0.67 g, 58%).... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cc[nH]c1.c1ccccc1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | null | null | Cc1c(CO)c[nH]c1-c1ccccc1F>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC>Cc1c(C=O)c[nH]c1-c1ccccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17120af9b4a04753ad993beb7837ed9f | C=CC(=O)OC.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>>COC(=O)c1cc[nH]c1 | O.C1(=CC=C(C=C1)S(=O)(=O)C[N+]#[C-])C.C(C=C)(=O)OC.CC(C)([O-])C.[K+]>>N1C=C(C=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].Cc1ccc(S(=O)(=O)[CH2:9][N+:8]#[C-:7])cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][nH:8][cH:9]1 | C=CC(=O)OC.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | COC(=O)c1cc[nH]c1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 39f0e003eef39c7768a0aede59e10369c1ebccc1bda2d76e3203ad0a59895e73 | e567b76b877c19b5a87c7a266da83a842334b0d3d7ff4a9ba0538fc9f1773f7f | c1cc[nH]c1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[N+;H0;D2:2]#[C-;H0;D1:3]):c:c:1.[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH2;D1;+0:9]>>[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:3]:[nH;D2;+0:2]:[cH;D2;+0:1]:1 | 41 | [{"value": 41.0, "product": "N1C=C(C=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of potassium tert-butoxide (17.9 g) in tetrahydrofuran (200 mL) was added dropwise a solution of p-toluenesulfonylmethyl isocyanide (25.2 g) and methyl acrylate (11.8 mL) in tetrahydrofuran (200 mL) over 30 min. The reaction mixture was stirred at room temperature for 1 hr, water was added, and the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ester.Isocyanide.Vinyl | Ester | c1ccccc1 | c1cc[nH]c1 | c1cc[nH]c1 | TsOH.HO- | O1CCCC1 | null | 1 | C=CC(=O)OC.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>O1CCCC1>COC(=O)c1cc[nH]c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65f0efdf9d5c4c9099481cd387e4cbe3 | C/C=C/C(=O)OC.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>>COC(=O)c1c[nH]cc1C | CC(C)([O-])C.[K+].C1(=CC=C(C=C1)S(=O)(=O)C[N+]#[C-])C.C(\C=C\C)(=O)OC>>CC=1C(=CNC1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:9]/[CH3:10].Cc1ccc(S(=O)(=O)[CH2:6][N+:7]#[C-:8])cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][cH:8][c:9]1[CH3:10] | C/C=C/C(=O)OC.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | COC(=O)c1c[nH]cc1C | null | null | null | Functional Group Interconversion | OtherReaction | 222aa38425ebd527cae949f4f6a41b16a79f5bedc3b38d407b2efba1132a0002 | 2b254751295ab0c58d4be59c7dc1148a5e0af4419b8080ba37410673480117ee | c1cc[nH]c1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[N+;H0;D2:2]#[C-;H0;D1:3]):c:c:1.[C;D1;H3:4]/[CH;D2;+0:5]=[CH;D2;+0:6]/[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]>>[C;D1;H3:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:3]:[nH;D2;+0:2]:[cH;D2;+0:1]:[c;H0;D3;+0:6]:1-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10] | 25 | [{"value": 25.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 19 and using p-toluenesulfonylmethyl isocyanide (94.6 g), methyl crotonate (48.5 g) and potassium tert-butoxide (76.7 g), the title compound was obtained as a pale-yellow solid (yield 16.8 g, 25%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ester.Isocyanide | Ester | c1ccccc1 | c1cc[nH]c1 | c1cc[nH]c1 | TsOH.HO- | null | null | null | C/C=C/C(=O)OC.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>>COC(=O)c1c[nH]cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8906695c0511400ab6aa653e9d58e236 | C=COC(C)=O.CCOC(=O)CC(C)=O.N>>CCOC(=O)c1cc[nH]c1C | N.C(C)(=O)OC=C.BrBr.O=C(CC(=O)OCC)C>>CC=1NC=CC1C(=O)OCC | CC(=O)O[CH:8]=[CH2:7].O=[C:10]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:11].[NH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][nH:9][c:10]1[CH3:11] | C=COC(C)=O.CCOC(=O)CC(C)=O.N | CCOC(=O)c1cc[nH]c1C | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 2633cdec1426893628fe136129d1edcddc4b21c65927a590f43ab5196c42f086 | f397f35add667cd2079cc0f5c10fd9068989f947555f4b5ec67f80071ec94898 | c1cc[nH]c1 | C-C(=O)-O-[CH;D2;+0:1]=[CH2;D1;+0:2].O=[C;H0;D3;+0:3](-[C;D1;H3:4])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[NH3;D0;+0:10]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c;H0;D3;+0:5]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[nH;D2;+0:10]:[c;H0;D3;+0:3]:1-[C;D1;H3:4] | 35 | [{"value": 35.0, "product": "CC=1NC=CC1C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Vinyl acetate (13.4 g) was added dropwise over 2 hr to bromine (25 g) under ice-cooling with stirring. The reaction mixture was further stirred at the same temperature for 1 hr. Ethyl 3-oxobutanoate (18.5 g) was added, and 25% aqueous ammonia solution (44 mL) was added dropwise over 1 hr. The reaction mixture was furth... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester.Vinyl | Ester | null | c1cc[nH]c1 | c1cc[nH]c1 | HO- | O | null | null | C=COC(C)=O.CCOC(=O)CC(C)=O.N>O>CCOC(=O)c1cc[nH]c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a6eeb3c376c4a268630653acdd2cd34 | COC(=O)c1cc[nH]c1.O=C1CCC(=O)N1Br>>COC(=O)c1c[nH]c(Br)c1 | N1C=C(C=C1)C(=O)OC.BrN1C(CCC1=O)=O.O>>BrC1=CC(=CN1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][cH:8][cH:10]1.O=C1CCC(=O)N1[Br:9]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]([Br:9])[cH:10]1 | COC(=O)c1cc[nH]c1.O=C1CCC(=O)N1Br | COC(=O)c1c[nH]c(Br)c1 | null | N1=CC=CC=C1 | O1CCCC1 | Functional Group Interconversion | Bromination | 40ba41cd9c6955f8bb4a47b285f327e8347ac41f3539d665e8b27d9300f356ae | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1cc[nH]c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[cH;D2;+0:7]:[#7;a:8]:[c:9]:1>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[c;H0;D3;+0:7](-[Br;H0;D1;+0:1]):[#7;a:8]:[c:9]:1 | 62 | [{"value": 62.0, "product": "BrC1=CC(=CN1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.7, "product": "BrC1=CC(=CN1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution (30 mL) of methyl 1H-pyrrole-3-carboxylate (3.06 g) in tetrahydrofuran was cooled to −78° C., N-bromosuccinimide (4.38 g) and then pyridine (3 drops) were added, and the mixture was stirred at the same temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cc[nH]c1.C1CCNC1 | c1cc[nH]c1 | c1cc[nH]c1 | HO- | N1=CC=CC=C1.O1CCCC1 | null | 1 | COC(=O)c1cc[nH]c1.O=C1CCC(=O)N1Br>N1=CC=CC=C1.O1CCCC1>COC(=O)c1c[nH]c(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-904e584988244852b2ce443b7b421560 | COC(=O)c1c[nH]cc1C.O=C1CCC(=O)N1Br>>COC(=O)c1c[nH]c(Br)c1C | CC=1C(=CNC1)C(=O)OC.BrN1C(CCC1=O)=O>>BrC1=C(C(=CN1)C(=O)OC)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][cH:8][c:10]1[CH3:11].O=C1CCC(=O)N1[Br:9]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8]([Br:9])[c:10]1[CH3:11] | COC(=O)c1c[nH]cc1C.O=C1CCC(=O)N1Br | COC(=O)c1c[nH]c(Br)c1C | null | null | null | Functional Group Interconversion | Bromination | 40ba41cd9c6955f8bb4a47b285f327e8347ac41f3539d665e8b27d9300f356ae | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1cc[nH]c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[#7;a:7]:[cH;D2;+0:8]:[c:9]:1-[C;D1;H3:10]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[#7;a:7]:[c;H0;D3;+0:8](-[Br;H0;D1;+0:1]):[c:9]:1-[C;D1;H3:10] | 31 | [{"value": 31.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 22 and using methyl 4-methyl-1H-pyrrole-3-carboxylate (1.0 g) and N-bromosuccinimide (1.28 g), the title compound was obtained as a pale-yellow solid (yield 489 mg, 31%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cc[nH]c1.C1CCNC1 | c1cc[nH]c1 | c1cc[nH]c1 | HO- | null | null | null | COC(=O)c1c[nH]cc1C.O=C1CCC(=O)N1Br>>COC(=O)c1c[nH]c(Br)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f6a8a451cf94b50be7fa1ea2b7f6126 | CCOC(=O)c1cc[nH]c1C.O=C1CCC(=O)N1Br>>CCOC(=O)c1cc(Br)[nH]c1C | O.C(C)OCC.CC=1NC=CC1C(=O)OCC.BrN1C(CCC1=O)=O>>BrC1=CC(=C(N1)C)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][nH:10][c:11]1[CH3:12].O=C1CCC(=O)N1[Br:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([Br:9])[nH:10][c:11]1[CH3:12] | CCOC(=O)c1cc[nH]c1C.O=C1CCC(=O)N1Br | CCOC(=O)c1cc(Br)[nH]c1C | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | 40ba41cd9c6955f8bb4a47b285f327e8347ac41f3539d665e8b27d9300f356ae | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1cc[nH]c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[#7;a:7]:[cH;D2;+0:8]:[c:9]:1>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[#7;a:7]:[c;H0;D3;+0:8](-[Br;H0;D1;+0:1]):[c:9]:1 | 97.5 | [{"value": 97.0, "product": "BrC1=CC(=C(N1)C)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.5, "product": "BrC1=CC(=C(N1)C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of ethyl 2-methyl-1H-pyrrole-3-carboxylate (1.53 g) in tetrahydrofuran (20 mL) was added N-bromosuccinimide (1.78 g) at −78° C., and the mixture was stirred at the same temperature for 30 min. Water and diethyl ether were added to extract the reaction mixture. The extract was washed with saturated brine, ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cc[nH]c1.C1CCNC1 | c1cc[nH]c1 | c1cc[nH]c1 | HO- | O1CCCC1 | null | 0.5 | CCOC(=O)c1cc[nH]c1C.O=C1CCC(=O)N1Br>O1CCCC1>CCOC(=O)c1cc(Br)[nH]c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e377dbb240c4fa980e16805795d7559 | O=P(Cl)(Cl)Cl.O=S(=O)(O)c1cccnc1>>O=S(=O)(Cl)c1cccnc1 | Cl.N1=CC(=CC=C1)S(=O)(=O)O.P(Cl)(Cl)(Cl)(Cl)Cl.P(=O)(Cl)(Cl)Cl>>Cl.N1=CC(=CC=C1)S(=O)(=O)Cl | O=P(Cl)(Cl)[Cl:5].O[S:3](=[O:2])(=[O:4])[c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1>>[O:2]=[S:3](=[O:4])([Cl:5])[c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1 | O=P(Cl)(Cl)Cl.O=S(=O)(O)c1cccnc1 | O=S(=O)(Cl)c1cccnc1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | c1ccncc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[Cl;H0;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 81 | [{"value": 81.0, "product": "Cl.N1=CC(=CC=C1)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 8 | HOUR | A mixture of 3-pyridinesulfonic acid (50.0 g), phosphorus pentachloride (80.0 g) and phosphorus oxychloride (100 mL) was stirred at 120° C. for 8 hr. Under a nitrogen atmosphere, the mixture was cooled to room temperature, and chloroform (dehydrated, 330 mL) was added. Hydrogen chloride was blown in, and the precipitat... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | c1ccncc1 | HCl | C(Cl)(Cl)Cl | 120 | 8 | O=P(Cl)(Cl)Cl.O=S(=O)(O)c1cccnc1>C(Cl)(Cl)Cl>O=S(=O)(Cl)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-685b563a3f044c4c814e1a24381beab1 | COc1ccc(N)cn1.Cl.O=S=O>>COc1ccc(S(=O)(=O)Cl)cn1 | S(=O)=O.NC=1C=CC(=NC1)OC.Cl.N(=O)[O-].[Na+]>>COC1=CC=C(C=N1)S(=O)(=O)Cl | N[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:12][cH:11]1.[ClH:10].[S:7](=[O:8])=[O:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[Cl:10])[cH:11][n:12]1 | COc1ccc(N)cn1.Cl.O=S=O | COc1ccc(S(=O)(=O)Cl)cn1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | d44a4364e5511e440a48fb914cbd59017338faff430f0e7127e14fae8b0eff0a | 49dcc8f7b4471977f8fe724b4dd774612c303d853f75a373d5b25cc7ccd4c205 | c1ccncc1 | N-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[ClH;D0;+0:7].[O;D1;H0:8]=[S;H0;D2;+0:9]=[O;D1;H0:10]>>[Cl;H0;D1;+0:7]-[S;H0;D4;+0:9](=[O;D1;H0:8])(=[O;D1;H0:10])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 51 | [{"value": 51.0, "product": "COC1=CC=C(C=N1)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Amino-2-methoxypyridine (1.24 g) was dissolved in acetic acid (8.3 mL), and the mixture was stirred under ice-cooling. Concentrated hydrochloric acid (8.3 mL) was added, and an aqueous solution (5 mL) of sodium nitrite (689 mg) was added dropwise over 15 min while keeping the inside temperature at not higher than 10°... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonyl halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | C(C)(=O)O | null | null | COc1ccc(N)cn1.Cl.O=S=O>C(C)(=O)O>COc1ccc(S(=O)(=O)Cl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-156979b5ed7b42a69b0af40d5cec0cb0 | Cl.Nc1ccc(Cl)nc1.O=S=O>>O=S(=O)(Cl)c1ccc(Cl)nc1 | N(=O)[O-].[Na+].NC=1C=CC(=NC1)Cl.Cl.S(=O)=O>>ClC1=CC=C(C=N1)S(=O)(=O)Cl | [ClH:4].N[c:5]1[cH:6][cH:7][c:8]([Cl:9])[n:10][cH:11]1.[O:1]=[S:2]=[O:3]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[n:10][cH:11]1 | Cl.Nc1ccc(Cl)nc1.O=S=O | O=S(=O)(Cl)c1ccc(Cl)nc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d44a4364e5511e440a48fb914cbd59017338faff430f0e7127e14fae8b0eff0a | 49dcc8f7b4471977f8fe724b4dd774612c303d853f75a373d5b25cc7ccd4c205 | c1ccncc1 | N-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[ClH;D0;+0:7].[O;D1;H0:8]=[S;H0;D2;+0:9]=[O;D1;H0:10]>>[Cl;H0;D1;+0:7]-[S;H0;D4;+0:9](=[O;D1;H0:8])(=[O;D1;H0:10])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 58 | [{"value": 58.0, "product": "ClC1=CC=C(C=N1)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice-cooling, thionyl chloride (12 mL) was added dropwise over 1 hr to water (70 mL) and the mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, under ice-cooling, 5-amino-2-chloropyridine (5.0 g) was added to concentrated hydrochloric acid (40 mL) and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonyl halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | null | null | null | Cl.Nc1ccc(Cl)nc1.O=S=O>>O=S(=O)(Cl)c1ccc(Cl)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35d51a9a1d2749fc9c60ce097cc97ef4 | Cl.Nc1cccnc1Cl.O=S=O>>O=S(=O)(Cl)c1cccnc1Cl | N(=O)[O-].[Na+].NC=1C(=NC=CC1)Cl.Cl.S(=O)=O>>ClC1=NC=CC=C1S(=O)(=O)Cl | [ClH:4].N[c:5]1[cH:6][cH:7][cH:8][n:9][c:10]1[Cl:11].[O:1]=[S:2]=[O:3]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][cH:8][n:9][c:10]1[Cl:11] | Cl.Nc1cccnc1Cl.O=S=O | O=S(=O)(Cl)c1cccnc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d44a4364e5511e440a48fb914cbd59017338faff430f0e7127e14fae8b0eff0a | 49dcc8f7b4471977f8fe724b4dd774612c303d853f75a373d5b25cc7ccd4c205 | c1ccncc1 | N-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[ClH;D0;+0:8].[O;D1;H0:9]=[S;H0;D2;+0:10]=[O;D1;H0:11]>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[S;H0;D4;+0:10](-[Cl;H0;D1;+0:8])(=[O;D1;H0:9])=[O;D1;H0:11] | 42 | [{"value": 42.0, "product": "ClC1=NC=CC=C1S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice-cooling, thionyl chloride (24 mL) was added dropwise over 1 hr to water (140 mL) and the mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, under ice-cooling, 3-amino-2-chloropyridine (10 g) was added to concentrated hydrochloric acid (80 mL) and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonyl halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | null | null | null | Cl.Nc1cccnc1Cl.O=S=O>>O=S(=O)(Cl)c1cccnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-870c5c31dd374e4eb91f07bbaff0a4e0 | Cc1cc([N+](=O)[O-])cnc1Cl>>Cc1cc(N)cnc1Cl | [Cl-].[NH4+].ClC1=NC=C(C=C1C)[N+](=O)[O-]>>ClC1=C(C=C(C=N1)N)C | O=[N+:5]([O-])[c:4]1[cH:3][c:2]([CH3:1])[c:8]([Cl:9])[n:7][cH:6]1>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:6][n:7][c:8]1[Cl:9] | Cc1cc([N+](=O)[O-])cnc1Cl | Cc1cc(N)cnc1Cl | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccncc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 42 | [{"value": 42.0, "product": "ClC1=C(C=C(C=N1)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.5, "product": "ClC1=C(C=C(C=N1)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Reduced iron (793 mg) was added to an aqueous solution (25 mL) of ammonium chloride (1.27 g), and the mixture was stirred at room temperature for 5 min. A solution (10 mL) of 2-chloro-3-methyl-5-nitropyridine (816 mg) in methanol was added dropwise over 10 min. The reaction mixture was stirred at 40° C. for 20 min and ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1 | Other | CO | null | 0.083333 | Cc1cc([N+](=O)[O-])cnc1Cl>CO>Cc1cc(N)cnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7ea0e95dd0b44798fc29a0b9c8d4253 | Cc1cc(N)cnc1Cl.Cl.O=S=O>>Cc1cc(S(=O)(=O)Cl)cnc1Cl | S(=O)=O.ClC1=C(C=C(C=N1)N)C.Cl.N(=O)[O-].[Na+]>>ClC1=C(C=C(C=N1)S(=O)(=O)Cl)C | N[c:4]1[cH:3][c:2]([CH3:1])[c:11]([Cl:12])[n:10][cH:9]1.[ClH:8].[S:5](=[O:6])=[O:7]>>[CH3:1][c:2]1[cH:3][c:4]([S:5](=[O:6])(=[O:7])[Cl:8])[cH:9][n:10][c:11]1[Cl:12] | Cc1cc(N)cnc1Cl.Cl.O=S=O | Cc1cc(S(=O)(=O)Cl)cnc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d44a4364e5511e440a48fb914cbd59017338faff430f0e7127e14fae8b0eff0a | 49dcc8f7b4471977f8fe724b4dd774612c303d853f75a373d5b25cc7ccd4c205 | c1ccncc1 | N-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[ClH;D0;+0:7].[O;D1;H0:8]=[S;H0;D2;+0:9]=[O;D1;H0:10]>>[Cl;H0;D1;+0:7]-[S;H0;D4;+0:9](=[O;D1;H0:8])(=[O;D1;H0:10])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 62 | [{"value": 62.0, "product": "ClC1=C(C=C(C=N1)S(=O)(=O)Cl)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice-cooling, thionyl chloride (0.6 mL) was added dropwise over 30 min to water (3.4 mL). The mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, under ice-cooling, 6-chloro-5-methylpyridine-3-amine (278 mg) was added to concentrated hydrochloric acid (6 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonyl halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | null | null | null | Cc1cc(N)cnc1Cl.Cl.O=S=O>>Cc1cc(S(=O)(=O)Cl)cnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef15361f7a62441d899e6da0afee91eb | O=S(=O)(O)O.Sc1ccccn1.[O-]Cl>>O=S(=O)(Cl)c1ccccn1 | SC1=NC=CC=C1.S(O)(O)(=O)=O.Cl[O-].[Na+]>>N1=C(C=CC=C1)S(=O)(=O)Cl | O=S(O)(O)=[O:3].[SH:2][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1.[O-:1][Cl:4]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1 | O=S(=O)(O)O.Sc1ccccn1.[O-]Cl | O=S(=O)(Cl)c1ccccn1 | null | null | O | Oxidation | OtherReaction | 9785de8c4af497b47fef775da94901f552247c79b12446361bd1c0f569fb21a2 | 00ceeb3b5a6ffef49234435732248538ad1b48dd29750ec1526974fa138e885a | c1ccncc1 | O-S(-O)(=O)=[O;H0;D1;+0:1].[Cl;H0;D1;+0:2]-[O-;H0;D1:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[Cl;H0;D1;+0:2]-[S;H0;D4;+0:4](=[O;H0;D1;+0:3])(=[O;H0;D1;+0:1])-[c:5](:[c:6]):[#7;a:7]:[c:8] | 77 | [{"value": 77.0, "product": "N1=C(C=CC=C1)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice-cooling, 2-mercaptopyridine (2.0 g) was added to sulfuric acid (50 mL) and the mixture was stirred. Sodium hypochlorite solution (chlorine content 5%, 126 mL) was added dropwise over 1.5 hr, and the mixture was further stirred at the same temperature for 30 min. The reaction mixture was diluted with water (10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Sulfonyl halide | null | null | c1ccncc1 | HO- | O | null | null | O=S(=O)(O)O.Sc1ccccn1.[O-]Cl>O>O=S(=O)(Cl)c1ccccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0800cd075b74b94b7340e01104e400e | CCOC(=O)c1c[nH]c(-c2ccccc2)c1.O=S(=O)(F)c1ccc(Cl)nn1>>CCOC(=O)c1cc(-c2ccccc2)n(S(=O)(=O)c2cccnn2)c1 | ClC1=CC=C(N=N1)S(=O)(=O)F.C(O)([O-])=O.[Na+].C1COCCOCCOCCOCCO1.[H-].[Na+].NN.C1(=CC=CC=C1)C1=CC(=CN1)C(=O)OCC>>C1(=CC=CC=C1)C1=CC(=CN1S(=O)(=O)C=1N=NC=CC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[nH:15][cH:25]1.F[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][c:22](Cl)[n:23][n:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[n:15]([S:16](=[O:17])(=[O:18])[c:19]2[cH:20]... | CCOC(=O)c1c[nH]c(-c2ccccc2)c1.O=S(=O)(F)c1ccc(Cl)nn1 | CCOC(=O)c1cc(-c2ccccc2)n(S(=O)(=O)c2cccnn2)c1 | null | null | O1CCCC1 | Acylation | OtherReaction | a029c3e19ecd4bb7a8b7eda76bd36682476a6f6535504b6e2764312ea6c234fc | 3d2c04f63ac9e2f3df734bfe73fabc984c30969d75ff1d2ce6780c93e45e2f3f | O=S(=O)(c1cccnn1)n1cccc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4](-[S;H0;D4;+0:5](-F)(=[O;D1;H0:6])=[O;D1;H0:7]):[c:8]:[c:9]:1.[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[c:14]:[nH;D2;+0:15]:[c:16](-[c:17]):[c:18]:1>>[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[c:14]:[n;H0;D3;+0:15](-[S;H0;D4;+0:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:4]2:[#7;a:3]:[#7;a:2]:[... | 34.8 | [{"value": 24.0, "product": "C1(=CC=CC=C1)C1=CC(=CN1S(=O)(=O)C=1N=NC=CC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.8, "product": "C1(=CC=CC=C1)C1=CC(=CN1S(=O)(=O)C=1N=NC=CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Ethyl 5-phenyl-1H-pyrrole-3-carboxylate (1.06 g) was dissolved in tetrahydrofuran (30 mL), sodium hydride (60% in oil, 300 mg) was added and the mixture was stirred at room temperature for 15 min. 15-Crown-5 (1.52 mL) was added and the mixture was further stirred at the same temperature for 15 min. 6-Chloropyridazine-3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Sulfonyl halide | null | c1cc[nH]c1.c1ccnnc1 | c1cc[nH]c1.c1ccnnc1 | c1cc[nH]c1.c1ccccc1.c1ccnnc1 | Other | O1CCCC1 | null | 0.25 | CCOC(=O)c1c[nH]c(-c2ccccc2)c1.O=S(=O)(F)c1ccc(Cl)nn1>O1CCCC1>CCOC(=O)c1cc(-c2ccccc2)n(S(=O)(=O)c2cccnn2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0cd5a3f20ee49d6aab74a710f332afe | CCOC(=O)c1cc[nH]c1C.O=S(=O)(Cl)c1ccccc1>>CCOC(=O)c1ccn(S(=O)(=O)c2ccccc2)c1C | C1(=CC=CC=C1)S(=O)(=O)Cl.CC=1NC=CC1C(=O)OCC.[H-].[Na+]>>CC=1N(C=CC1C(=O)OCC)S(=O)(=O)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][nH:9][c:19]1[CH3:20].Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][n:9]([S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]1[CH3:20] | CCOC(=O)c1cc[nH]c1C.O=S(=O)(Cl)c1ccccc1 | CCOC(=O)c1ccn(S(=O)(=O)c2ccccc2)c1C | null | null | null | Acylation | OtherReaction | 40c00ec44b7af41885dbd1ffd066e14223cf28d90060492536c6496a8e914910 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1ccccc1)n1cccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[nH;D2;+0:13]:[c:14]:1-[C;D1;H3:15]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[c:12]:[n;H0;D3;+0:13](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]):[c:14]:1-[C;D1;H3:15] | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 41 and using ethyl 2-methyl-1H-pyrrole-3-carboxylate (8.81 g), sodium hydride (60% in oil, 2.58 g) and benzenesulfonyl chloride (7.8 mL), the title compound was obtained as white crystals (yield 14.3 g, 85%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1.c1ccccc1 | HCl | null | null | null | CCOC(=O)c1cc[nH]c1C.O=S(=O)(Cl)c1ccccc1>>CCOC(=O)c1ccn(S(=O)(=O)c2ccccc2)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51b0a26a2bbc4d6f88a66fbda2f9cd5c | CCOC(=O)c1cc(Br)[nH]c1C.O=S(=O)(Cl)c1cccnc1>>CCOC(=O)c1cc(Br)n(S(=O)(=O)c2cccnc2)c1C | Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.BrC1=CC(=C(N1)C)C(=O)OCC.[H-].[Na+].C(O)([O-])=O.[Na+].C1COCCOCCOCCOCCO1>>BrC1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([Br:9])[nH:10][c:20]1[CH3:21].Cl[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([Br:9])[n:10]([S:11](=[O:12])(=[O:13])[c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)[c:20]1[CH3:21] | CCOC(=O)c1cc(Br)[nH]c1C.O=S(=O)(Cl)c1cccnc1 | CCOC(=O)c1cc(Br)n(S(=O)(=O)c2cccnc2)c1C | null | null | O1CCCC1 | Acylation | OtherReaction | 40c00ec44b7af41885dbd1ffd066e14223cf28d90060492536c6496a8e914910 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14](-[Br;D1;H0:15]):[nH;D2;+0:16]:[c:17]:1-[C;D1;H3:18]>>[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14](-[Br;D1;H0:15]):[n;H0;D3;+0:16](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[... | 64 | [{"value": 64.0, "product": "BrC1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.6, "product": "BrC1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Ethyl 5-bromo-2-methyl-1H-pyrrole-3-carboxylate (2.26 g) was dissolved in tetrahydrofuran (100 mL), sodium hydride (60% in oil, 1.16 g) was added and the mixture was stirred at room temperature for 15 min. 15-Crown-5 (5.90 mL) was added and the mixture was further stirred at the same temperature for 15 min. 3-Pyridines... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1.c1ccncc1 | HCl | O1CCCC1 | null | 0.25 | CCOC(=O)c1cc(Br)[nH]c1C.O=S(=O)(Cl)c1cccnc1>O1CCCC1>CCOC(=O)c1cc(Br)n(S(=O)(=O)c2cccnc2)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b113a56f9294f2abf9dabf6e5fcda88 | CCOC(=O)c1cc(Br)n(S(=O)(=O)c2cccnc2)c1C.OB(O)c1ccccc1>>CCOC(=O)c1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2)c1C | BrC1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C)C(=O)OCC.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].O>>CC=1N(C(=CC1C(=O)OCC)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1 | Br[c:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:25]([CH3:26])[n:15]1[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1.OB(O)[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[n:15]([S:16](=[O:17])(=[O:18])[c:... | CCOC(=O)c1cc(Br)n(S(=O)(=O)c2cccnc2)c1C.OB(O)c1ccccc1 | CCOC(=O)c1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2)c1C | null | null | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | b2d7c68422e63d91324e9f95cf31db744bedd9bd92be56bb43ec6d6dd2e086c2 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[#7;a:8]:1-[#16:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#16:9]-[#7;a:8]1:[c:7]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14] | 106.6 | [{"value": 100.0, "product": "CC=1N(C(=CC1C(=O)OCC)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.6, "product": "CC=1N(C(=CC1C(=O)OCC)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 40 | MINUTE | A suspension of ethyl 5-bromo-2-methyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carboxylate (2.26 g), phenylboronic acid (1.54 g), dichloro[bis(triphenylphosphine)]palladium (211 mg) and sodium carbonate (1.91 g) in 1,2-dimethoxyethane (20 mL)-water (10 mL) was stirred at 80° C. for 40 min. After cooling, the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1c[nH]cc1.c1ccccc1 | c1c[nH]cc1.c1ccccc1 | c1c[nH]cc1.c1ccccc1.c1ccncc1 | HBr.B | COCCOC | 80 | 0.666667 | CCOC(=O)c1cc(Br)n(S(=O)(=O)c2cccnc2)c1C.OB(O)c1ccccc1>COCCOC>CCOC(=O)c1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7ce408ff2a7a4fad8ca77311f2254f40 | COC(=O)c1cc(Br)n(S(=O)(=O)c2ccccc2)c1>>O=S(=O)(c1ccccc1)n1cc(CO)cc1Br | Cl.[H-].C(C(C)C)[Al+]CC(C)C.BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C(=O)OC>>BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)CO | CO[C:13]([c:12]1[cH:11][n:10]([S:2](=[O:1])(=[O:3])[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:16]([Br:17])[cH:15]1)=[O:14]>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[n:10]1[cH:11][c:12]([CH2:13][OH:14])[cH:15][c:16]1[Br:17] | COC(=O)c1cc(Br)n(S(=O)(=O)c2ccccc2)c1 | O=S(=O)(c1ccccc1)n1cc(CO)cc1Br | null | null | O1CCCC1.C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=S(=O)(c1ccccc1)n1cccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[#7;a:5](-[#16:6]):[c:7]:[c:8]:1>>[#16:6]-[#7;a:5]1:[c:4]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:8]:[c:7]:1 | 108.9 | [{"value": 100.0, "product": "BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 108.9, "product": "BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | A solution (80 mL) of methyl 5-bromo-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate (7.1 g) in tetrahydrofuran was cooled to −78° C., a 1.5 mol/L solution (42 mL) of diisobutylaluminum hydride in toluene was added dropwise over 30 min and the mixture was further stirred at −78° C. for 1 hr. 1 mol/L hydrochloric acid (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1cc[nH]c1 | Other | O1CCCC1.C1(=CC=CC=C1)C | -78 | 1 | COC(=O)c1cc(Br)n(S(=O)(=O)c2ccccc2)c1>O1CCCC1.C1(=CC=CC=C1)C>O=S(=O)(c1ccccc1)n1cc(CO)cc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d33ad461f684e69859d49638e5ac872 | CCOC(=O)c1ccn(S(=O)(=O)c2ccccc2)c1C>>Cc1c(CO)ccn1S(=O)(=O)c1ccccc1 | CC=1N(C=CC1C(=O)OCC)S(=O)(=O)C1=CC=CC=C1.C1(=CC=CC=C1)C.[H-].C(C(C)C)[Al+]CC(C)C>>CC=1N(C=CC1CO)S(=O)(=O)C1=CC=CC=C1 | CCO[C:4]([c:3]1[c:2]([CH3:1])[n:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:7][cH:6]1)=[O:5]>>[CH3:1][c:2]1[c:3]([CH2:4][OH:5])[cH:6][cH:7][n:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CCOC(=O)c1ccn(S(=O)(=O)c2ccccc2)c1C | Cc1c(CO)ccn1S(=O)(=O)c1ccccc1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=S(=O)(c1ccccc1)n1cccc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[#16:7]):[c:8]:1-[C;D1;H3:9]>>[#16:7]-[#7;a:6]1:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:8]:1-[C;D1;H3:9] | 96 | [{"value": 96.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 13 and using ethyl 2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate (8.05 g) and 1.5 mol/L diisobutylaluminum hydride toluene solution (55 mL), the title compound was obtained as white crystals (yield 6.61 g, 96%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1c[nH]cc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1ccn(S(=O)(=O)c2ccccc2)c1C>>Cc1c(CO)ccn1S(=O)(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35771c8ef4bf4af6a1e4fe3ca0060164 | O=S(=O)(c1ccccc1)n1cc(CO)cc1Br>>O=Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1 | BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)CO.O.C[N+]1(CCOCC1)[O-]>>BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C=O | [OH:1][CH2:2][c:3]1[cH:4][c:5]([Br:6])[n:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([Br:6])[n:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1 | O=S(=O)(c1ccccc1)n1cc(CO)cc1Br | O=Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | C(C)#N | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=S(=O)(c1ccccc1)n1cccc1 | [#16:1]-[#7;a:2]1:[c:3]:[c:4](-[CH2;D2;+0:5]-[OH;D1;+0:6]):[c:7]:[c:8]:1>>[#16:1]-[#7;a:2]1:[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7]:[c:8]:1 | 71 | [{"value": 71.0, "product": "BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.2, "product": "BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution (80 mL) of [5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol (7.1 g) in acetonitrile were added tetra-n-propylammonium perruthenate (0.63 g), N-methylmorpholine N-oxide hydrate (4.2 g) and molecular sieves 4A powder (3.5 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cc[nH]c1.c1ccccc1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(C)#N | null | 2 | O=S(=O)(c1ccccc1)n1cc(CO)cc1Br>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(C)#N>O=Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cef4b78ee4f94aa9ab2bc95d72810267 | Cc1c(C=O)cn(S(=O)(=O)c2ccccc2)c1Br.OB(O)c1ccccc1>>Cc1c(C=O)c[nH]c1-c1ccccc1 | BrC1=C(C(=CN1S(=O)(=O)C1=CC=CC=C1)C=O)C.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>>CC=1C(=CNC1C1=CC=CC=C1)C=O | O=S(=O)(c1ccccc1)[n:7]1[cH:6][c:3]([CH:4]=[O:5])[c:2]([CH3:1])[c:8]1Br.OB(O)[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][nH:7][c:8]1-[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | Cc1c(C=O)cn(S(=O)(=O)c2ccccc2)c1Br.OB(O)c1ccccc1 | Cc1c(C=O)c[nH]c1-c1ccccc1 | null | null | O.COCCOC | C-C Coupling | OtherReaction | 10cbc4045254db5758344435c8b38bca11a334689db1f09754719c83db557e43 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc[nH]2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:[n;H0;D3;+0:8]:1-S(=O)(=O)-c1:c:c:c:c:c:1.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C;D1;H3:3]-[c:2]1:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:[nH;D2;+0:8]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 81.1 | [{"value": 69.0, "product": "CC=1C(=CNC1C1=CC=CC=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.1, "product": "CC=1C(=CNC1C1=CC=CC=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | HOUR | A suspension of 5-bromo-4-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (1.78 g), phenylboronic acid (1.37 g), dichloro[bis(triphenylphosphine)]palladium (0.19 g) and sodium carbonate (1.72 g) in 1,2-dimethoxyethane (30 mL)-water (10 mL) was stirred at 100° C. for 1 hr. 8 mol/L aqueous sodium hydroxide solution (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | HBr.B | O.COCCOC | 100 | 1 | Cc1c(C=O)cn(S(=O)(=O)c2ccccc2)c1Br.OB(O)c1ccccc1>O.COCCOC>Cc1c(C=O)c[nH]c1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-018c2b5f131e41e688d594a36866654a | Cc1c(CO)ccn1S(=O)(=O)c1ccccc1>>Cc1c(C=O)ccn1S(=O)(=O)c1ccccc1 | CC=1N(C=CC1CO)S(=O)(=O)C1=CC=CC=C1.CS(=O)C.C(O)([O-])=O.[Na+]>>CC=1N(C=CC1C=O)S(=O)(=O)C1=CC=CC=C1 | [CH3:1][c:2]1[c:3]([CH2:4][OH:5])[cH:6][cH:7][n:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][cH:7][n:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | Cc1c(CO)ccn1S(=O)(=O)c1ccccc1 | Cc1c(C=O)ccn1S(=O)(=O)c1ccccc1 | null | null | C(C)N(CC)CC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=S(=O)(c1ccccc1)n1cccc1 | [#16:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5](-[CH2;D2;+0:6]-[OH;D1;+0:7]):[c:8]:1-[C;D1;H3:9]>>[#16:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):[c:8]:1-[C;D1;H3:9] | 84 | [{"value": 84.0, "product": "CC=1N(C=CC1C=O)S(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "CC=1N(C=CC1C=O)S(=O)(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a mixture of [2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol (6.35 g), dimethyl sulfoxide (50 mL) and triethylamine (25 mL) was added sulfur trioxide-pyridine complex (4.57 g), and the mixture was stirred at room temperature for 12 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1c[nH]cc1.c1ccccc1 | null | C(C)N(CC)CC | null | 12 | Cc1c(CO)ccn1S(=O)(=O)c1ccccc1>C(C)N(CC)CC>Cc1c(C=O)ccn1S(=O)(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c951f45b1dc459f9763ed1bcc0b6ad9 | Cc1[nH]ccc1C=O.O=S(=O)(Cl)c1cccnc1>>Cc1c(C=O)ccn1S(=O)(=O)c1cccnc1 | C1COCCOCCOCCOCCO1.CC=1NC=CC1C=O.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.[H-].[Na+]>>CC=1N(C=CC1C=O)S(=O)(=O)C=1C=NC=CC1 | [CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][cH:7][nH:8]1.Cl[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][cH:7][n:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1 | Cc1[nH]ccc1C=O.O=S(=O)(Cl)c1cccnc1 | Cc1c(C=O)ccn1S(=O)(=O)c1cccnc1 | null | null | null | Acylation | OtherReaction | 40c00ec44b7af41885dbd1ffd066e14223cf28d90060492536c6496a8e914910 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[C;D1;H3:9]-[c:10]1:[nH;D2;+0:11]:[c:12]:[c:13]:[c:14]:1-[C:15]=[O;D1;H0:16]>>[C;D1;H3:9]-[c:10]1:[c:14](-[C:15]=[O;D1;H0:16]):[c:13]:[c:12]:[n;H0;D3;+0:11]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8] | 44 | [{"value": 44.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar reaction as in Reference Example 44 and using 2-methyl-1H-pyrrole-3-carbaldehyde (1.10 g), sodium hydride (60% in oil, 1.20 g), 15-crown-5 (6.0 mL) and pyridin-3-ylsulfonyl chloride hydrochloride (3.22 g), the title compound was obtained as white crystals (yield 1.10 g, 44%).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1.c1ccncc1 | HCl | null | null | null | Cc1[nH]ccc1C=O.O=S(=O)(Cl)c1cccnc1>>Cc1c(C=O)ccn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96d7ec4598274ba8b48a578f1317ae81 | Cc1c(C=O)ccn1S(=O)(=O)c1cccnc1.O=C1CCC(=O)N1Br>>Cc1c(C=O)cc(Br)n1S(=O)(=O)c1cccnc1 | O.CC=1N(C=CC1C=O)S(=O)(=O)C=1C=NC=CC1.BrN1C(CCC1=O)=O>>BrC1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C)C=O | [CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][cH:7][n:9]1[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1.O=C1CCC(=O)N1[Br:8]>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][c:7]([Br:8])[n:9]1[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1 | Cc1c(C=O)ccn1S(=O)(=O)c1cccnc1.O=C1CCC(=O)N1Br | Cc1c(C=O)cc(Br)n1S(=O)(=O)c1cccnc1 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 45b120e1defda7dfd188f9d58cce4a0f02402540683f8cdf07342faf62007b1f | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=S(=O)(c1cccnc1)n1cccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#16:2]-[#7;a:3]1:[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[cH;D2;+0:9]:1>>[#16:2]-[#7;a:3]1:[c:4]:[c:5](-[C:6]=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9]:1-[Br;H0;D1;+0:1] | 53 | [{"value": 53.0, "product": "BrC1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.7, "product": "BrC1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-methyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (974 mg) in N,N-dimethylformamide (10 mL) was added N-bromosuccinimide (1.17 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1c[nH]cc1.C1CCNC1 | c1c[nH]cc1 | c1c[nH]cc1.c1ccncc1 | HO- | CN(C=O)C | null | 1 | Cc1c(C=O)ccn1S(=O)(=O)c1cccnc1.O=C1CCC(=O)N1Br>CN(C=O)C>Cc1c(C=O)cc(Br)n1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8883f4baabdf435fb16a13bff4a40aa2 | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1cccnc1>>O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2)c1 | Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.[H-].[Na+].C1(=CC=CC=C1)C1=CC(=CN1)C=O.C1COCCOCCOCCOCCO1>>C1(=CC=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[nH:12][cH:22]1.Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12]([S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][n:20][cH:21]2)[cH:22]1 | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1cccnc1 | O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2)c1 | null | null | O1CCCC1.C(C)(=O)OCC | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:13]1:[c:12]:[c:11](-[C:10]=[O;D1;H0:9]):[c:16]:[c:14]:1-[c:15] | 75.3 | [{"value": 75.0, "product": "C1(=CC=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.3, "product": "C1(=CC=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under an argon atmosphere, 5-phenyl-1H-pyrrole-3-carbaldehyde (342 mg) was dissolved in absolute tetrahydrofuran (20 mL) and sodium hydride (60% in oil, 240 mg) was added while stirring at room temperature. After stirring at the same temperature for 15 min, 15-crown-5 (1.21 mL) was added, and the mixture was further st... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1.C(C)(=O)OCC | null | null | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1cccnc1>O1CCCC1.C(C)(=O)OCC>O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0cd100819cde4f4a8f826c6ad1e8d796 | COc1ccc(S(=O)(=O)Cl)cn1.O=Cc1c[nH]c(-c2ccccc2)c1>>COc1ccc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2)cn1 | COC1=CC=C(C=N1)S(=O)(=O)Cl.[H-].[Na+].C1(=CC=CC=C1)C1=CC(=CN1)C=O.C1COCCOCCOCCOCCO1>>COC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O | Cl[S:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:24][cH:23]1)(=[O:8])=[O:9].[nH:10]1[cH:11][c:12]([CH:13]=[O:14])[cH:15][c:16]1-[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[n:10]2[cH:11][c:12]([CH:13]=[O:14])[cH:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:2... | COc1ccc(S(=O)(=O)Cl)cn1.O=Cc1c[nH]c(-c2ccccc2)c1 | COc1ccc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2)cn1 | null | null | O1CCCC1.C(C)(=O)OCC | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[n;H0;D3;+0:13](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]):[c:14](-[c:15]):[c:16]:1 | 17.3 | [{"value": 17.0, "product": "COC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.3, "product": "COC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under an argon atmosphere, 5-phenyl-1H-pyrrole-3-carbaldehyde (171 mg) was dissolved in absolute tetrahydrofuran (20 mL), and sodium hydride (60% in oil, 200 mg) was added at room temperature while stirring. After stirring at the same temperature for 15 min, 15-crown-5 (1.01 mL) was added, and the mixture was further s... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccncc1.c1cc[nH]c1.c1ccccc1 | HCl | O1CCCC1.C(C)(=O)OCC | null | null | COc1ccc(S(=O)(=O)Cl)cn1.O=Cc1c[nH]c(-c2ccccc2)c1>O1CCCC1.C(C)(=O)OCC>COc1ccc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02f779fe96b849acbc03beab8e2869c6 | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1ccc(Cl)nc1>>O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(Cl)nc2)c1 | ClC1=CC=C(C=N1)S(=O)(=O)Cl.[H-].[Na+].C1(=CC=CC=C1)C1=CC(=CN1)C=O.C1COCCOCCOCCOCCO1>>ClC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[nH:12][cH:23]1.Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][c:19]([Cl:20])[n:21][cH:22]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12]([S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([Cl:20])[n:21][cH:22]2)[c... | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1ccc(Cl)nc1 | O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(Cl)nc2)c1 | null | null | O1CCCC1.C(C)(=O)OCC | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:13]1:[c:12]:[c:11](-[C:10]=[O;D1;H0:9]):[c:16]:[c:14]:1-[c:15] | 73.2 | [{"value": 73.0, "product": "ClC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.2, "product": "ClC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under an argon atmosphere, 5-phenyl-1H-pyrrole-3-carbaldehyde (514 mg) was dissolved in absolute tetrahydrofuran (15 mL), and sodium hydride (60% in oil, 180 mg) was added at room temperature while stirring. After stirring at the same temperature for 15 min, 15-crown-5 (0.90 mL) was added, and the mixture was further s... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1.C(C)(=O)OCC | null | null | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1ccc(Cl)nc1>O1CCCC1.C(C)(=O)OCC>O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(Cl)nc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e0b5aee549d487391ae6476f97e5172 | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1cccnc1Cl>>O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2Cl)c1 | ClC1=NC=CC=C1S(=O)(=O)Cl.C1(=CC=CC=C1)C1=CC(=CN1)C=O.[H-].[Na+].C1COCCOCCOCCOCCO1>>ClC1=NC=CC=C1S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[nH:12][cH:23]1.Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][n:20][c:21]1[Cl:22]>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12]([S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][n:20][c:21]2[Cl:22])[cH:23... | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1cccnc1Cl | O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2Cl)c1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6](-[Cl;D1;H0:7]):[#7;a:8]:[c:9].[O;D1;H0:10]=[C:11]-[c:12]1:[c:13]:[nH;D2;+0:14]:[c:15](-[c:16]):[c:17]:1>>[Cl;D1;H0:7]-[c:6](:[#7;a:8]:[c:9]):[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[n;H0;D3;+0:14]1:[c:13]:[c:12](-[C:11]=[O;D1;H0:10]):[c:17]:[c:... | null | [] | null | null | null | null | By a reaction under similar conditions as in Reference Example 55 and using 5-phenyl-1H-pyrrole-3-carbaldehyde (514 mg), sodium hydride (60% in oil, 180 mg), 15-crown-5 (0.90 mL) and 2-chloro-3-pyridinesulfonyl chloride (716 mg), the title compound was obtained as an amorphous form (yield 716 mg, 69%).
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | null | null | null | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1cccnc1Cl>>O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd5280fdfbd64f9bb1ebe55519466ff3 | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1cnc(Cl)nc1>>O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cnc(Cl)nc2)c1 | C1COCCOCCOCCOCCO1.C1(=CC=CC=C1)C1=CC(=CN1)C=O.ClC1=NC=C(C=N1)S(=O)(=O)Cl.[H-].[Na+]>>ClC1=NC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[nH:12][cH:23]1.Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][n:18][c:19]([Cl:20])[n:21][cH:22]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12]([S:13](=[O:14])(=[O:15])[c:16]2[cH:17][n:18][c:19]([Cl:20])[n:21][cH:22]2)[cH:... | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1cnc(Cl)nc1 | O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cnc(Cl)nc2)c1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cncnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1.[O;D1;H0:10]=[C:11]-[c:12]1:[c:13]:[nH;D2;+0:14]:[c:15](-[c:16]):[c:17]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4]1:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1)-[n;H0;D3;+0:14]1:[c:13]:[c:12](-[C:11]=[O;D1;H0:10]):[c:17]:[c:15]... | 56 | [{"value": 56.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a reaction under similar conditions as in Reference Example 55 and using 5-phenyl-1H-pyrrole-3-carbaldehyde (342 mg), sodium hydride (60% in oil, 120 mg), 15-crown-5 (0.60 mL) and 2-chloro-5-pyrimidinesulfonyl chloride (554 mg), the title compound was obtained as a yellow solid (yield 390 mg, 56%).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1cncnc1 | HCl | null | null | null | O=Cc1c[nH]c(-c2ccccc2)c1.O=S(=O)(Cl)c1cnc(Cl)nc1>>O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cnc(Cl)nc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a78abdc8a174bba9efafa4a8504c9ec | Cc1cc(S(=O)(=O)Cl)cnc1Cl.O=Cc1c[nH]c(-c2ccccc2)c1>>Cc1cc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2)cnc1Cl | C1COCCOCCOCCOCCO1.C1(=CC=CC=C1)C1=CC(=CN1)C=O.ClC1=C(C=C(C=N1)S(=O)(=O)Cl)C.[H-].[Na+]>>ClC1=C(C=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O)C | Cl[S:5]([c:4]1[cH:3][c:2]([CH3:1])[c:23]([Cl:24])[n:22][cH:21]1)(=[O:6])=[O:7].[nH:8]1[cH:9][c:10]([CH:11]=[O:12])[cH:13][c:14]1-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][c:2]1[cH:3][c:4]([S:5](=[O:6])(=[O:7])[n:8]2[cH:9][c:10]([CH:11]=[O:12])[cH:13][c:14]2-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21]... | Cc1cc(S(=O)(=O)Cl)cnc1Cl.O=Cc1c[nH]c(-c2ccccc2)c1 | Cc1cc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2)cnc1Cl | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[nH;D2;+0:15]:[c:16]:1>>[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[n;H0;D3;+0:15](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]):[c:16]:1 | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a reaction under similar conditions as in Reference Example 55 and using 5-phenyl-1H-pyrrole-3-carbaldehyde (171 mg), sodium hydride (60% in oil, 60 mg), 15-crown-5 (0.30 mL) and 6-chloro-5-methylpyridine-3-sulfonyl chloride (270 mg), the title compound was obtained as a solid (yield 244 mg, 68%).
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccncc1.c1cc[nH]c1.c1ccccc1 | HCl | null | null | null | Cc1cc(S(=O)(=O)Cl)cnc1Cl.O=Cc1c[nH]c(-c2ccccc2)c1>>Cc1cc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2)cnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d2fc4d0769542a1ab87ba3f39834d78 | CCOC(=O)c1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2)c1C>>Cc1c(C=O)cc(-c2ccccc2)n1S(=O)(=O)c1cccnc1 | [H-].C(C(C)C)[Al+]CC(C)C.CC=1N(C(=CC1C(=O)OCC)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1.O.C(C)(=O)OCC>>CC=1N(C(=CC1C=O)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1 | CCO[C:4]([c:3]1[c:2]([CH3:1])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:6]1)=[O:5]>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22]... | CCOC(=O)c1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2)c1C | Cc1c(C=O)cc(-c2ccccc2)n1S(=O)(=O)c1cccnc1 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[#16:7]):[c:8]:1-[C;D1;H3:9]>>[#16:7]-[#7;a:6]1:[c:5]:[c:4]:[c:3](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:8]:1-[C;D1;H3:9] | 27.2 | [{"value": 27.0, "product": "CC=1N(C(=CC1C=O)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.2, "product": "CC=1N(C(=CC1C=O)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A solution (15 mL) of ethyl 2-methyl-5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carboxylate (980 mg) in tetrahydrofuran was cooled to −78° C., a 1.5 mol/L solution (5.3 mL) of diisobutylaluminum hydride in toluene was added dropwise over 10 min., and the mixture was warmed to 0° C. over 2 hr. Water (100 mL) and eth... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1c[nH]cc1.c1ccccc1.c1ccncc1 | HO- | O1CCCC1.C1(=CC=CC=C1)C | 0 | 0.5 | CCOC(=O)c1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2)c1C>O1CCCC1.C1(=CC=CC=C1)C>Cc1c(C=O)cc(-c2ccccc2)n1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e56ba46b9794e88b28e4147955ece9c | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1cccnc1>>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1 | Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.C1COCCOCCOCCOCCO1.FC1=C(C=CC=C1)C1=CC(=CN1)C=O.[H-].[Na+]>>FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[nH:13][cH:23]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[cH:23]1 | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1cccnc1 | O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1 | null | null | O1CCCC1.[Cl-].[Na+].O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:13]1:[c:12]:[c:11](-[C:10]=[O;D1;H0:9]):[c:16]:[c:14]:1-[c:15] | 82 | [{"value": 82.0, "product": "FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution (96 mL) of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (475 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 503 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (2.77 g) was added dropwise and the mixture was stirred for 30 min. Pyridine-3-sulfonyl chloride hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1.[Cl-].[Na+].O | null | 0.5 | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1cccnc1>O1CCCC1.[Cl-].[Na+].O>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9787ac34004545eead5ce2fc3ff2242f | O=Cc1c[nH]c(-c2ccccc2C(F)(F)F)c1.O=S(=O)(Cl)c1cccnc1>>O=Cc1cc(-c2ccccc2C(F)(F)F)n(S(=O)(=O)c2cccnc2)c1 | Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.C1COCCOCCOCCOCCO1.FC(C1=C(C=CC=C1)C1=CC(=CN1)C=O)(F)F.[H-].[Na+]>>N1=CC(=CC=C1)S(=O)(=O)N1C=C(C=C1C1=C(C=CC=C1)C(F)(F)F)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[nH:16][cH:26]1.Cl[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12]([F:13])([F:14])[F:15])[n:16]([S:17](=[O:18])(=[O:19])[c:20]2... | O=Cc1c[nH]c(-c2ccccc2C(F)(F)F)c1.O=S(=O)(Cl)c1cccnc1 | O=Cc1cc(-c2ccccc2C(F)(F)F)n(S(=O)(=O)c2cccnc2)c1 | null | null | O1CCCC1.[Cl-].[Na+].O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:13]1:[c:12]:[c:11](-[C:10]=[O;D1;H0:9]):[c:16]:[c:14]:1-[c:15] | 100 | [{"value": 100.0, "product": "N1=CC(=CC=C1)S(=O)(=O)N1C=C(C=C1C1=C(C=CC=C1)C(F)(F)F)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "N1=CC(=CC=C1)S(=O)(=O)N1C=C(C=C1C1=C(C=CC=C1)C(F)(F)F)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution (36 mL) of 5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde (240 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 201 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (1.11 g) was added dropwise and the mixture was stirred for 30 min. Pyridine-3-sulfonyl chlori... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1.[Cl-].[Na+].O | null | 0.5 | O=Cc1c[nH]c(-c2ccccc2C(F)(F)F)c1.O=S(=O)(Cl)c1cccnc1>O1CCCC1.[Cl-].[Na+].O>O=Cc1cc(-c2ccccc2C(F)(F)F)n(S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46a73add8daf40348c260d6bdccbd28d | Cc1c(C=O)c[nH]c1-c1ccccc1.O=S(=O)(Cl)c1cccnc1>>Cc1c(C=O)cn(S(=O)(=O)c2cccnc2)c1-c1ccccc1 | Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.[H-].[Na+].CC=1C(=CNC1C1=CC=CC=C1)C=O.C1COCCOCCOCCOCCO1>>CC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C=O | [CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][nH:7][c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][n:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:... | Cc1c(C=O)c[nH]c1-c1ccccc1.O=S(=O)(Cl)c1cccnc1 | Cc1c(C=O)cn(S(=O)(=O)c2cccnc2)c1-c1ccccc1 | null | null | O1CCCC1.O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[nH;D2;+0:15]:[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:15]1:[c:16]:[c:11](-[C:10]=[O;D1;H0:9]):[c:12]:[c:13]:1-[c:14] | 53 | [{"value": 53.0, "product": "CC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.8, "product": "CC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 4-Methyl-5-phenyl-1H-pyrrole-3-carbaldehyde (185 mg) was dissolved in tetrahydrofuran (10 mL), sodium hydride (60% in oil, 60 mg) was added and the mixture was stirred at room temperature for 15 min. 15-Crown-5 (0.30 mL) was added and the mixture was further stirred at the same temperature for 15 min. 3-Pyridinesulfony... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1.c1ccccc1 | HCl | O1CCCC1.O | null | 0.25 | Cc1c(C=O)c[nH]c1-c1ccccc1.O=S(=O)(Cl)c1cccnc1>O1CCCC1.O>Cc1c(C=O)cn(S(=O)(=O)c2cccnc2)c1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-886f6cc7c36942c7934f749e5e49fb9b | Cc1c(C=O)c[nH]c1-c1ccccc1.O=S(=O)(Cl)c1ccccn1>>Cc1c(C=O)cn(S(=O)(=O)c2ccccn2)c1-c1ccccc1 | N1=C(C=CC=C1)S(=O)(=O)Cl.CC=1C(=CNC1C1=CC=CC=C1)C=O.[H-].[Na+].C1COCCOCCOCCOCCO1>>CC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C1=NC=CC=C1)C=O | [CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][nH:7][c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][n:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][n:16]2)[c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:... | Cc1c(C=O)c[nH]c1-c1ccccc1.O=S(=O)(Cl)c1ccccn1 | Cc1c(C=O)cn(S(=O)(=O)c2ccccn2)c1-c1ccccc1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1ccccn1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[O;D1;H0:8]=[C:9]-[c:10]1:[c:11]:[c:12](-[c:13]):[nH;D2;+0:14]:[c:15]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[#7;a:6]:[c:7])-[n;H0;D3;+0:14]1:[c:15]:[c:10](-[C:9]=[O;D1;H0:8]):[c:11]:[c:12]:1-[c:13] | null | [] | null | null | null | null | By a reaction under similar conditions as in Reference Example 65 and using 4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde (185 mg), sodium hydride (60% in oil, 60 mg), 15-crown-5 (0.30 mL) and 2-pyridinesulfonyl chloride (231 mg) instead of 3-pyridinesulfonyl chloride hydrochloride, the title compound was obtained as an ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1.c1ccccc1 | HCl | null | null | null | Cc1c(C=O)c[nH]c1-c1ccccc1.O=S(=O)(Cl)c1ccccn1>>Cc1c(C=O)cn(S(=O)(=O)c2ccccn2)c1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06fbdbda795c41b9a710b107226f7644 | Cc1c(C=O)c[nH]c1-c1ccccc1.Cc1nc(S(=O)(=O)Cl)cn1C>>Cc1c(C=O)cn(S(=O)(=O)c2cn(C)c(C)n2)c1-c1ccccc1 | C1COCCOCCOCCOCCO1.CC=1C(=CNC1C1=CC=CC=C1)C=O.CN1C(=NC(=C1)S(=O)(=O)Cl)C.[H-].[Na+]>>CN1C(=NC(=C1)S(=O)(=O)N1C=C(C(=C1C1=CC=CC=C1)C)C=O)C | [CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][nH:7][c:18]1-[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][n:13]([CH3:14])[c:15]([CH3:16])[n:17]1>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][n:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][n:13]([CH3:14])[c:15]([CH3:16])[n:17]2)[c:18]1-[c:19]1[cH:20][cH... | Cc1c(C=O)c[nH]c1-c1ccccc1.Cc1nc(S(=O)(=O)Cl)cn1C | Cc1c(C=O)cn(S(=O)(=O)c2cn(C)c(C)n2)c1-c1ccccc1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1c[nH]cn1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]:1.[O;D1;H0:10]=[C:11]-[c:12]1:[c:13]:[c:14](-[c:15]):[nH;D2;+0:16]:[c:17]:1>>[C;D1;H3:8]-[#7;a:7]1:[c:9]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[n;H0;D3;+0:16]2:[c:17]:[c:12](-[C:11]=[O;D1;H0:10]):[c:13]:[c:14]:2... | 86 | [{"value": 86.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a reaction under similar conditions as in Reference Example 65 and using 4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde (185 mg), sodium hydride (60% in oil, 60 mg), 15-crown-5 (0.30 mL) and (1,2-dimethyl-1H-imidazol-4-yl)sulfonyl chloride (253 mg), the title compound was obtained as a colorless solid (yield 294 mg, 86... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1c[nH]cn1.c1ccccc1 | HCl | null | null | null | Cc1c(C=O)c[nH]c1-c1ccccc1.Cc1nc(S(=O)(=O)Cl)cn1C>>Cc1c(C=O)cn(S(=O)(=O)c2cn(C)c(C)n2)c1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eaf0169436754701ae6ff1e949eba783 | Cc1c(C=O)c[nH]c1-c1ccccc1.Cc1nn(C)c(Cl)c1S(=O)(=O)Cl>>Cc1nn(C)c(Cl)c1S(=O)(=O)n1cc(C=O)c(C)c1-c1ccccc1 | C1COCCOCCOCCOCCO1.CC=1C(=CNC1C1=CC=CC=C1)C=O.ClC1=C(C(=NN1C)C)S(=O)(=O)Cl.[H-].[Na+]>>ClC1=C(C(=NN1C)C)S(=O)(=O)N1C=C(C(=C1C1=CC=CC=C1)C)C=O | [nH:12]1[cH:13][c:14]([CH:15]=[O:16])[c:17]([CH3:18])[c:19]1-[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.Cl[S:9]([c:8]1[c:2]([CH3:1])[n:3][n:4]([CH3:5])[c:6]1[Cl:7])(=[O:10])=[O:11]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([Cl:7])[c:8]1[S:9](=[O:10])(=[O:11])[n:12]1[cH:13][c:14]([CH:15]=[O:16])[c:17]([CH3:18])[c:19]1-[c:... | Cc1c(C=O)c[nH]c1-c1ccccc1.Cc1nn(C)c(Cl)c1S(=O)(=O)Cl | Cc1nn(C)c(Cl)c1S(=O)(=O)n1cc(C=O)c(C)c1-c1ccccc1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cn[nH]c1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[c:5](-[C;D1;H3:6]):[#7;a:7]:[#7;a:8](-[C;D1;H3:9]):[c:10]:1-[Cl;D1;H0:11].[O;D1;H0:12]=[C:13]-[c:14]1:[c:15]:[nH;D2;+0:16]:[c:17](-[c:18]):[c:19]:1>>[C;D1;H3:6]-[c:5]1:[#7;a:7]:[#7;a:8](-[C;D1;H3:9]):[c:10](-[Cl;D1;H0:11]):[c:4]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1... | 100 | [{"value": 100.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a reaction under similar conditions as in Reference Example 65 and using 4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde (185 mg), sodium hydride (60% in oil, 60 mg), 15-crown-5 (0.30 mL) and (5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)sulfonyl chloride (298 mg), the title compound was obtained as an oil (yield 379 mg, about... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cn[nH]c1.c1cc[nH]c1.c1ccccc1 | HCl | null | null | null | Cc1c(C=O)c[nH]c1-c1ccccc1.Cc1nn(C)c(Cl)c1S(=O)(=O)Cl>>Cc1nn(C)c(Cl)c1S(=O)(=O)n1cc(C=O)c(C)c1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-44a99158ff5c483593a6f5a68a2a423f | Cc1c(C=O)c[nH]c1-c1ccccc1.Cc1nc(C)c(S(=O)(=O)Cl)s1>>Cc1nc(C)c(S(=O)(=O)n2cc(C=O)c(C)c2-c2ccccc2)s1 | C1COCCOCCOCCOCCO1.CC=1C(=CNC1C1=CC=CC=C1)C=O.CC=1SC(=C(N1)C)S(=O)(=O)Cl.[H-].[Na+]>>CC=1SC(=C(N1)C)S(=O)(=O)N1C=C(C(=C1C1=CC=CC=C1)C)C=O | [nH:10]1[cH:11][c:12]([CH:13]=[O:14])[c:15]([CH3:16])[c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.Cl[S:7]([c:6]1[c:4]([CH3:5])[n:3][c:2]([CH3:1])[s:24]1)(=[O:8])=[O:9]>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([S:7](=[O:8])(=[O:9])[n:10]2[cH:11][c:12]([CH:13]=[O:14])[c:15]([CH3:16])[c:17]2-[c:18]2[cH:19][cH:20][cH:... | Cc1c(C=O)c[nH]c1-c1ccccc1.Cc1nc(C)c(S(=O)(=O)Cl)s1 | Cc1nc(C)c(S(=O)(=O)n2cc(C=O)c(C)c2-c2ccccc2)s1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cncs1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[C;D1;H3:9].[O;D1;H0:10]=[C:11]-[c:12]1:[c:13]:[nH;D2;+0:14]:[c:15](-[c:16]):[c:17]:1>>[C;D1;H3:9]-[c:8]1:[#7;a:7]:[c:6]:[#16;a:5]:[c:4]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[n;H0;D3;+0:14]1:[c:13]:[c:12](-[C:11]=[O;D1;H0:10])... | 8 | [{"value": 8.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a reaction under similar conditions as in Reference Example 65 and using 4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde (185 mg), sodium hydride (60% in oil, 60 mg), 15-crown-5 (0.30 mL) and (2,4-dimethyl-1,3-thiazol-5-yl)sulfonyl chloride (275 mg), the title compound was obtained as an oil (yield 27.8 mg, 8%).
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cscn1.c1cc[nH]c1.c1ccccc1 | HCl | null | null | null | Cc1c(C=O)c[nH]c1-c1ccccc1.Cc1nc(C)c(S(=O)(=O)Cl)s1>>Cc1nc(C)c(S(=O)(=O)n2cc(C=O)c(C)c2-c2ccccc2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f83347bc4d04a07bf983a37be4c26a8 | Cc1c(C=O)c[nH]c1-c1ccccc1F.O=S(=O)(Cl)c1cccnc1>>Cc1c(C=O)cn(S(=O)(=O)c2cccnc2)c1-c1ccccc1F | C1COCCOCCOCCOCCO1.FC1=C(C=CC=C1)C1=C(C(=CN1)C=O)C.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.[H-].[Na+]>>FC1=C(C=CC=C1)C1=C(C(=CN1S(=O)(=O)C=1C=NC=CC1)C=O)C | [CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][nH:7][c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[F:24].Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][n:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22... | Cc1c(C=O)c[nH]c1-c1ccccc1F.O=S(=O)(Cl)c1cccnc1 | Cc1c(C=O)cn(S(=O)(=O)c2cccnc2)c1-c1ccccc1F | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[nH;D2;+0:15]:[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:15]1:[c:16]:[c:11](-[C:10]=[O;D1;H0:9]):[c:12]:[c:13]:1-[c:14] | 87 | [{"value": 87.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 65 and using 5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carbaldehyde (301 mg), sodium hydride (60% in oil, 179 mg), 15-crown-5 (0.88 mL) and pyridin-3-ylsulfonyl chloride hydrochloride (476 mg), the title compound was obtained as white crystals (yield 440 mg, 87%).
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1.c1ccccc1 | HCl | null | null | null | Cc1c(C=O)c[nH]c1-c1ccccc1F.O=S(=O)(Cl)c1cccnc1>>Cc1c(C=O)cn(S(=O)(=O)c2cccnc2)c1-c1ccccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7cb62c60d9c9462399bccfcb0b15408b | C[NH3+].O=Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1>>CNCc1cc(Br)n(S(=O)(=O)c2ccccc2)c1 | BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C=O.[Cl-].C[NH3+].C(#N)[BH3-].[Na+]>>BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)CNC | [CH3:1][NH3+:2].O=[CH:3][c:4]1[cH:5][c:6]([Br:7])[n:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]([Br:7])[n:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | C[NH3+].O=Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1 | CNCc1cc(Br)n(S(=O)(=O)c2ccccc2)c1 | null | null | CO | Functional Group Interconversion | OtherReaction | f81a06fd4802217f2a89af56ed399b3c54f571141190aacbc8b18232a7f009a7 | 48e9cfa1233c86fcd1dbe33bcccd5760ec96958bf94448cbcdabe7d9b5e5da4f | O=S(=O)(c1ccccc1)n1cccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4](-[#16:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[NH3+;D1:9]>>[#16:5]-[#7;a:4]1:[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C;D1;H3:8]):[c:7]:[c:6]:1 | 120 | [{"value": 100.0, "product": "BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)CNC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 120.0, "product": "BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)CNC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution (60 mL) of 5-bromo-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (3.5 g) in methanol were added methylammonium chloride (7.5 g) and sodium cyanoborohydride (2.4 g), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary amine | null | null | c1cc[nH]c1.c1ccccc1 | HO- | CO | null | 1 | C[NH3+].O=Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1>CO>CNCc1cc(Br)n(S(=O)(=O)c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7911fa11974844c9a7a009b142ef8d80 | CNCc1cc(Br)n(S(=O)(=O)c2ccccc2)c1.O=C([O-])O>>CN(Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1)C(=O)OC(C)(C)C | C(O)([O-])=O.[Na+].BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)CNC>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C1=CC=CC=C1)=O | [CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]([Br:7])[n:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1.[O-][C:19](=[O:20])[OH:21]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]([Br:7])[n:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1)[C:19](=[O:20])[O:21][C:22]([CH3:23])(... | CNCc1cc(Br)n(S(=O)(=O)c2ccccc2)c1.O=C([O-])O | CN(Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1)C(=O)OC(C)(C)C | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | b60b7050648178cf87b8461a52efebd4094992e5bd847fac6aeeffea3f185375 | ed7cb4f05cf8979caa75e907f8c2b6171bb335392280c8fdecfa71b6334016ad | O=S(=O)(c1ccccc1)n1cccc1 | [#7;a:1]:[c:2]:[c:3]-[C:4]-[NH;D2;+0:5]-[C;D1;H3:6].[O-]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[#7;a:1]:[c:2]:[c:3]-[C:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13] | 73 | [{"value": 73.0, "product": "C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 1-[5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine (4.4 g) in ethyl acetate (60 mL) was added di-tert-butyl bicarbonate (2.8 mL), and the mixture was stirred at room temperature for 14 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Acid.Secondary amine | Carbamic ester.Ether.Boc | null | null | c1cc[nH]c1.c1ccccc1 | null | C(C)(=O)OCC | null | 14 | CNCc1cc(Br)n(S(=O)(=O)c2ccccc2)c1.O=C([O-])O>C(C)(=O)OCC>CN(Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-838fdcdfc61a45edba58328afeb5994b | CN(Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1)C(=O)OC(C)(C)C>>CN(Cc1c[nH]c(Br)c1)C(=O)OC(C)(C)C | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C1=CC=CC=C1)=O.O>>C(C)(C)(C)OC(N(C)CC1=CNC(=C1)Br)=O | O=S(=O)(c1ccccc1)[n:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:9][c:7]1[Br:8]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]([Br:8])[cH:9]1)[C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | CN(Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1)C(=O)OC(C)(C)C | CN(Cc1c[nH]c(Br)c1)C(=O)OC(C)(C)C | null | null | O1CCCC1.CO.[OH-].[Na+] | Reduction | OtherReaction | e84bce0a3684cb001278a9df3f54235c2ecd212d7bfeaa59bdd53379604bae1d | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1cc[nH]c1 | O=S(=O)(-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1-[Br;D1;H0:6])-c1:c:c:c:c:c:1>>[Br;D1;H0:6]-[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 61 | [{"value": 61.0, "product": "C(C)(C)(C)OC(N(C)CC1=CNC(=C1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.9, "product": "C(C)(C)(C)OC(N(C)CC1=CNC(=C1)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | tert-Butyl{[5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (1.0 g) was dissolved in a mixed solvent of tetrahydrofuran (15 mL) and methanol (5 mL), and 8 mol/L aqueous sodium hydroxide solution (1.5 mL) was added dropwise at not more than 10° C. After stirring at the same temperature for 4 hr, water w... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1 | HO- | O1CCCC1.CO.[OH-].[Na+] | null | 4 | CN(Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1)C(=O)OC(C)(C)C>O1CCCC1.CO.[OH-].[Na+]>CN(Cc1c[nH]c(Br)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f567915120c41ecac6c3480e343b4f5 | CN(Cc1c[nH]c(Br)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1>>CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | [H-].[Na+].C(C)(C)(C)OC(N(C)CC1=CNC(=C1)Br)=O.C1COCCOCCOCCOCCO1.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O | [CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]([Br:7])[nH:8][cH:18]1)[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25].Cl[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6]([Br:7])[n:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[cH:18]1)[C:19](=[... | CN(Cc1c[nH]c(Br)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | null | O1CCCC1.O.CN(C=O)C | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[Br;D1;H0:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[Br;D1;H0:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[n;H0;D3;+0:14]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8] | 85.6 | [{"value": 85.0, "product": "C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a suspension (10 mL) of sodium hydride (60% in oil, 204 mg) in tetrahydrofuran was added a solution (3 mL) of tert-butyl[(5-bromo-1H-pyrrol-3-yl)methyl]methylcarbamate (410 mg) in N,N-dimethylformamide at 0° C., and 15-crown-5 (938 mg) and pyridin-3-ylsulfonyl chloride hydrochloride (456 mg) were added at the same t... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1 | HCl | O1CCCC1.O.CN(C=O)C | null | 2 | CN(Cc1c[nH]c(Br)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1>O1CCCC1.O.CN(C=O)C>CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eeaa97d24a5346f09f7478792a7aca8a | CN.Cc1cc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2)cnc1Cl.O=C([O-])O>>Cc1cc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2ccccc2)cnc1Cl | C(O)([O-])=O.[Na+].CN.[BH4-].[Na+].ClC1=C(C=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O)C>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC(=C(C1)C)Cl)=O | [NH2:12][CH3:13].O=[CH:11][c:10]1[cH:9][n:8]([S:5]([c:4]2[cH:3][c:2]([CH3:1])[c:31]([Cl:32])[n:30][cH:29]2)(=[O:6])=[O:7])[c:22](-[c:23]2[cH:24][cH:25][cH:26][cH:17][cH:28]2)[cH:21]1.[O-][C:14](=[O:15])[OH:16]>>[CH3:1][c:2]1[cH:3][c:4]([S:5](=[O:6])(=[O:7])[n:8]2[cH:9][c:10]([CH2:11][N:12]([CH3:13])[C:14](=[O:15])[O:16... | CN.Cc1cc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2)cnc1Cl.O=C([O-])O | Cc1cc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2ccccc2)cnc1Cl | null | null | O1CCCC1.O.CO | C-C Coupling | OtherReaction | 3b707e34799ac6851d60bdaa66c51532260299fc603a1d0d55ae2ba7ff1616a1 | 3d8ce2b92b61290a79a351e04280a781726e579e49920cac71c26ad6abac8497 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[c:5]2:[c:6]:[c:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:2):[#7;a:11](-[#16:12]):[c:13]:1.[C;D1;H3:14]-[NH2;D1;+0:15].[O-]-[C;H0;D3;+0:16](=[O;D1;H0:17])-[OH;D1;+0:18]>>[#16:12]-[#7;a:11]1:[c:13]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:15](-[C;D1;H3:14])-[C;H0;D3;+0:16](=[O;D1;H0:17])-[O;H... | 77 | [{"value": 77.0, "product": "C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC(=C(C1)C)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 1-[(6-Chloro-5-methylpyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde (244 mg) was dissolved in absolute tetrahydrofuran (6.8 mL), a 2 mol/L solution (0.34 mL) of methylamine in tetrahydrofuran was added, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was added to a solution of ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbonic Acid.Primary amine | Carbamic ester.Ether.Boc | c1ccccc1 | c1ccccc1 | c1ccncc1.c1cc[nH]c1.c1ccccc1 | null | O1CCCC1.O.CO | null | 4 | CN.Cc1cc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2)cnc1Cl.O=C([O-])O>O1CCCC1.O.CO>Cc1cc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2ccccc2)cnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2b7ee5d4bb54cf1a931f04cc07087a8 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccsc1>>CN(Cc1cc(-c2ccsc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.S1C=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CSC=C1)S(=O)(=O)C=1C=NC=CC1 | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:22][n:12]1[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1.OB(O)[c:7]1[cH:8][cH:9][s:10][cH:11]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][s:10][cH:11]2)[n:12]([S:13](=[O:14])(=[O:15])... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccsc1 | CN(Cc1cc(-c2ccsc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 487361cf9c8a098c20bfd7c2c5754120927e29e3849a70b2ee791c6972a05de5 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccsc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#16;a:9]:[c:10]:[c:11]:1>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[#16;a:9]:[c:10]:[c:11]:1 | 81 | [{"value": 81.0, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CSC=C1)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CSC=C1)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 1 | HOUR | Under an argon atmosphere, a suspension of tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (232 mg), 3-thienylboronic acid (138 mg), tetrakis(triphenylphosphine)palladium (31.3 mg) and sodium carbonate (175 mg) in 1,2-dimethoxyethane (10 mL) and water (5 mL) was stirred at 105° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccsc1 | c1cc[nH]c1.c1ccsc1 | c1cc[nH]c1.c1ccsc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 105 | 1 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccsc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>CN(Cc1cc(-c2ccsc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f60495c664e94c12b0a0e88622c77c5c | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1ccccc1B(O)O>>Cc1ccccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.CC1=C(C=CC=C1)B(O)O>>CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=C(C=CC=C1)C)S(=O)(=O)C=1C=NC=CC1 | Br[c:8]1[cH:9][c:10]([CH2:11][N:12]([CH3:13])[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][n:22]1[S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1.OB(O)[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]([CH2:11][N:12]([CH3:13]... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1ccccc1B(O)O | Cc1ccccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C;D1;H3:11]):[c:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C;D1;H3:11]):[c:12] | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (2-methylphenyl)boronic acid (190 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (222 mg), the title compound was obtained as a pale-yellow o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1ccccc1B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>Cc1ccccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1fc61714612e45bb8256116c5181e5ee | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1ccccc1B(O)O>>Cc1ccccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.CC1=C(C=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=C(C=CC=C1)C)S(=O)(=O)C=1C=NC=CC1 | Br[c:8]1[cH:9][c:10]([CH2:11][N:12]([CH3:13])[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][n:22]1[S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1.OB(O)[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]([CH2:11][N:12]([CH3:13]... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1ccccc1B(O)O | Cc1ccccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C;D1;H3:11]):[c:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C;D1;H3:11]):[c:12] | 68.2 | [{"value": 68.0, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=C(C=CC=C1)C)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.2, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=C(C=CC=C1)C)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 18 | HOUR | By a similar operation as in Reference Example 79 and using tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (2-methylphenyl)boronic acid (190 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (222 mg), the title compound was obtained as a pale-yellow o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 105 | 18 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1ccccc1B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>Cc1ccccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-729bc652f32b40d28d6d8220e77c1f60 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1cc(F)ccc1B(O)O>>Cc1cc(F)ccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.FC1=CC(=C(C=C1)B(O)O)C>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=C(C=C(C=C1)F)C)S(=O)(=O)C=1C=NC=CC1)=O | Br[c:9]1[cH:10][c:11]([CH2:12][N:13]([CH3:14])[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][n:23]1[S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][cH:30][n:31][cH:32]1.OB(O)[c:8]1[c:2]([CH3:1])[cH:3][c:4]([F:5])[cH:6][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]([CH2:12][... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1cc(F)ccc1B(O)O | Cc1cc(F)ccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C;D1;H3:11]):[c:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C;D1;H3:11]):[c:12] | 67 | [{"value": 67.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (4-fluoro-2-methylphenyl)boronic acid (215 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (222 mg), the title compound was obtained as a pale-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1cc(F)ccc1B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>Cc1cc(F)ccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa5c5ab6a9f841d3b3524f6130d63ef1 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1cscc1B(O)O>>Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.CC=1C(=CSC1)B(O)O>>CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CSC=C1C)S(=O)(=O)C=1C=NC=CC1 | Br[c:7]1[cH:8][c:9]([CH2:10][N:11]([CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][n:21]1[S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][cH:28][n:29][cH:30]1.OB(O)[c:6]1[c:2]([CH3:1])[cH:3][s:4][cH:5]1>>[CH3:1][c:2]1[cH:3][s:4][cH:5][c:6]1-[c:7]1[cH:8][c:9]([CH2:10][N:11]([CH3:12])[C:13](=[O:14])... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1cscc1B(O)O | Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | 487361cf9c8a098c20bfd7c2c5754120927e29e3849a70b2ee791c6972a05de5 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccsc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#16;a:9]:[c:10]:[c:11]:1-[C;D1;H3:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[#16;a:9]:[c:10]:[c:11]:1-[C;D1;H3:12] | 64 | [{"value": 64.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (4-methyl-3-thienyl)boronic acid (198 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (222 mg), the title compound was obtained as a pale-yello... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccsc1 | c1ccsc1.c1cc[nH]c1 | c1ccsc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1cscc1B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f683e154a2647dab4297b40fba6bd97 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1cscc1B(O)O>>Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.CC=1C(=CSC1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CSC=C1C)S(=O)(=O)C=1C=NC=CC1 | Br[c:7]1[cH:8][c:9]([CH2:10][N:11]([CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][n:21]1[S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][cH:28][n:29][cH:30]1.OB(O)[c:6]1[c:2]([CH3:1])[cH:3][s:4][cH:5]1>>[CH3:1][c:2]1[cH:3][s:4][cH:5][c:6]1-[c:7]1[cH:8][c:9]([CH2:10][N:11]([CH3:12])[C:13](=[O:14])... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1cscc1B(O)O | Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 487361cf9c8a098c20bfd7c2c5754120927e29e3849a70b2ee791c6972a05de5 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccsc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#16;a:9]:[c:10]:[c:11]:1-[C;D1;H3:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[#16;a:9]:[c:10]:[c:11]:1-[C;D1;H3:12] | 64.1 | [{"value": 64.0, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CSC=C1C)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.1, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CSC=C1C)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 18 | HOUR | By a similar operation as in Reference Example 79 and using tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (4-methyl-3-thienyl)boronic acid (198 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (222 mg), the title compound was obtained as a pale-yello... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccsc1 | c1ccsc1.c1cc[nH]c1 | c1ccsc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 105 | 18 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.Cc1cscc1B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c773ef10de904febbe70cd25be98166e | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.N#Cc1cccc(B(O)O)c1>>CN(Cc1cc(-c2cccc(C#N)c2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.C(#N)C=1C=C(C=CC1)B(O)O>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC(=CC=C1)C#N)S(=O)(=O)C=1C=NC=CC1)=O | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[cH:25][n:15]1[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([C:12]#[N:... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.N#Cc1cccc(B(O)O)c1 | CN(Cc1cc(-c2cccc(C#N)c2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | 94 | [{"value": 94.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (3-cyanophenyl)boronic acid (205 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (222 mg), the title compound was obtained as a pale-yellow oil... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.N#Cc1cccc(B(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1cc(-c2cccc(C#N)c2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c291a2317c484540b4455ca73f844837 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccccc1Cl>>CN(Cc1cc(-c2ccccc2Cl)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.ClC1=C(C=CC=C1)B(O)O>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=C(C=CC=C1)Cl)S(=O)(=O)C=1C=NC=CC1)=O | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[cH:24][n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Cl:13]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[Cl:13])[n:... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccccc1Cl | CN(Cc1cc(-c2ccccc2Cl)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[Cl;D1;H0:11]):[c:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[Cl;D1;H0:11]):[c:12] | 53 | [{"value": 53.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (2-chlorophenyl)boronic acid (218 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (222 mg), the title compound was obtained as a pale-blue oil ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccccc1Cl>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1cc(-c2ccccc2Cl)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-537e42143802433688494580d41cacc3 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccc(F)cc1F>>CN(Cc1c[nH]c(-c2ccc(F)cc2F)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.FC1=C(C=CC(=C1)F)B(O)O>>C(C)(C)(C)OC(N(C)CC1=CNC(=C1)C1=C(C=C(C=C1)F)F)=O | O=S(=O)(c1cccnc1)[n:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[cH:16][c:7]1Br.OB(O)[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]1[F:15]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][nH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[cH:16]1)[C:17](=[O:18])[O:19][C:... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccc(F)cc1F | CN(Cc1c[nH]c(-c2ccc(F)cc2F)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | OtherReaction | 091797deef34c648fc8f896a383f479af080cd2125994befadf3158dd8a13626 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc[nH]2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-S(=O)(=O)-c1:c:c:c:n:c:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[F;D1;H0:10]):[c:11]>>[F;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1):[c:7]:[c:8] | 50 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (2,4-difluorophenyl)boronic acid (198 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (220 mg), the title compound was obtained as a colorless ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccc(F)cc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1c[nH]c(-c2ccc(F)cc2F)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-778b1e581a6d487490d6d5b28bd756f2 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cc(F)ccc1F>>CN(Cc1c[nH]c(-c2cc(F)ccc2F)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.FC1=C(C=C(C=C1)F)B(O)O>>C(C)(C)(C)OC(N(C)CC1=CNC(=C1)C1=C(C=CC(=C1)F)F)=O | O=S(=O)(c1cccnc1)[n:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[cH:16][c:7]1Br.OB(O)[c:8]1[cH:9][c:10]([F:11])[cH:12][cH:13][c:14]1[F:15]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][nH:6][c:7](-[c:8]2[cH:9][c:10]([F:11])[cH:12][cH:13][c:14]2[F:15])[cH:16]1)[C:17](=[O:18])[O:19][C:... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cc(F)ccc1F | CN(Cc1c[nH]c(-c2cc(F)ccc2F)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | OtherReaction | 091797deef34c648fc8f896a383f479af080cd2125994befadf3158dd8a13626 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc[nH]2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-S(=O)(=O)-c1:c:c:c:n:c:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[F;D1;H0:10]):[c:11]>>[F;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1):[c:7]:[c:8] | 60 | [{"value": 60.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (2,5-difluorophenyl)boronic acid (220 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (220 mg), the title compound was obtained as a colorless ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cc(F)ccc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1c[nH]c(-c2cc(F)ccc2F)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6dfb6ae20ff4eccbcd8f38bf24e4808 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccc(Cl)cc1F>>CN(Cc1c[nH]c(-c2ccc(Cl)cc2F)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.ClC1=CC(=C(C=C1)B(O)O)F>>C(C)(C)(C)OC(N(C)CC1=CNC(=C1)C1=C(C=C(C=C1)Cl)F)=O | O=S(=O)(c1cccnc1)[n:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[cH:16][c:7]1Br.OB(O)[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[F:15]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][nH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]2[F:15])[cH:16]1)[C:17](=[O:18])[O:19][... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccc(Cl)cc1F | CN(Cc1c[nH]c(-c2ccc(Cl)cc2F)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | OtherReaction | 091797deef34c648fc8f896a383f479af080cd2125994befadf3158dd8a13626 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc[nH]2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-S(=O)(=O)-c1:c:c:c:n:c:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[F;D1;H0:10]):[c:11]>>[F;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1):[c:7]:[c:8] | 54 | [{"value": 54.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (4-chloro-2-fluorophenyl)boronic acid (243 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (220 mg), the title compound was obtained as a color... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccc(Cl)cc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1c[nH]c(-c2ccc(Cl)cc2F)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25e31368fc4742eeab8df861801592a1 | CN(Cc1c[nH]c(-c2ccc(F)cc2F)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1>>CN(Cc1cc(-c2ccc(F)cc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C1COCCOCCOCCOCCO1.C(C)(C)(C)OC(N(C)CC1=CNC(=C1)C1=C(C=C(C=C1)F)F)=O.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.[H-].[Na+]>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=C(C=C(C=C1)F)F)S(=O)(=O)C=1C=NC=CC1)=O | [CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]2[F:14])[nH:15][cH:25]1)[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32].Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]2[... | CN(Cc1c[nH]c(-c2ccc(F)cc2F)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1 | CN(Cc1cc(-c2ccc(F)cc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[c:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:14]1:[c:13]:[c:12]:[c:11]:[c:10]:1-[c:9] | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 44 and using tert-butyl{[5-(2,4-difluorophenyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (113 mg), sodium hydride (60% in oil, 51 mg), 15-crown-5 (0.21 mL) and pyridine-3-ylsulfonyl chloride hydrochloride (113 mg), the title compound was obtained as a pale-yellow oil (yield 1... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | null | null | null | CN(Cc1c[nH]c(-c2ccc(F)cc2F)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1>>CN(Cc1cc(-c2ccc(F)cc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-123e1f94be234b11acb7f52296716d61 | CN(Cc1c[nH]c(-c2cc(F)ccc2F)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1>>CN(Cc1cc(-c2cc(F)ccc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C1COCCOCCOCCOCCO1.C(C)(C)(C)OC(N(C)CC1=CNC(=C1)C1=C(C=CC(=C1)F)F)=O.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.[H-].[Na+]>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=C(C=CC(=C1)F)F)S(=O)(=O)C=1C=NC=CC1)=O | [CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]2[F:14])[nH:15][cH:25]1)[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32].Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]2[... | CN(Cc1c[nH]c(-c2cc(F)ccc2F)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1 | CN(Cc1cc(-c2cc(F)ccc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[c:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:14]1:[c:13]:[c:12]:[c:11]:[c:10]:1-[c:9] | 54 | [{"value": 54.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 44 and using tert-butyl{[5-(2,5-difluorophenyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (135 mg), sodium hydride (60% in oil, 60 mg), 15-crown-5 (0.25 mL) and pyridin-3-ylsulfonyl chloride hydrochloride (135 mg), the title compound was obtained as a colorless oil (yield 105 ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | null | null | null | CN(Cc1c[nH]c(-c2cc(F)ccc2F)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1>>CN(Cc1cc(-c2cc(F)ccc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3709138e248f4416a2c8559a917735b5 | CN(Cc1c[nH]c(-c2ccc(Cl)cc2F)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1>>CN(Cc1cc(-c2ccc(Cl)cc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C1COCCOCCOCCOCCO1.ClC1=CC(=C(C=C1)C1=CC(=CN1)CN(C(OC(C)(C)C)=O)C)F.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.[H-].[Na+]>>ClC1=CC(=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C)F | [CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]2[F:14])[nH:15][cH:25]1)[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32].Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]... | CN(Cc1c[nH]c(-c2ccc(Cl)cc2F)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1 | CN(Cc1cc(-c2ccc(Cl)cc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[c:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:14]1:[c:13]:[c:12]:[c:11]:[c:10]:1-[c:9] | 57 | [{"value": 57.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 44 and using tert-butyl {[5-(4-chloro-2-fluorophenyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (127 mg), sodium hydride (60% in oil, 54 mg), 15-crown-5 (0.22 mL) and pyridin-3-ylsulfonyl chloride hydrochloride (120 mg), the title compound was obtained as a colorless oil (yiel... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | null | null | null | CN(Cc1c[nH]c(-c2ccc(Cl)cc2F)c1)C(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccnc1>>CN(Cc1cc(-c2ccc(Cl)cc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96041b679b8d4334a31090cbd03cae3b | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cccc(F)c1>>CN(Cc1cc(-c2cccc(F)c2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)Br)S(=O)(=O)C=1C=NC=CC1)=O.FC=1C=C(C=CC1)B(O)O>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC(=CC=C1)F)S(=O)(=O)C=1C=NC=CC1)=O | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[cH:24][n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]2)[... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cccc(F)c1 | CN(Cc1cc(-c2cccc(F)c2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | 90 | [{"value": 90.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (300 mg), (3-fluorophenyl)boronic acid (195 mg), tetrakis(triphenylphosphine)palladium (40 mg) and sodium carbonate (222 mg), the title compound was obtained as a pale-yellow oi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cccc(F)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1cc(-c2cccc(F)c2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a333f877b8bd4db78a5049562ef794dd | BrBr.CC(=O)c1c(F)cccc1F>>O=C(CBr)c1c(F)cccc1F | O.BrBr.FC1=C(C(=CC=C1)F)C(C)=O.[Cl-].[Al+3].[Cl-].[Cl-]>>BrCC(=O)C1=C(C=CC=C1F)F | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[F:12]>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[F:12] | BrBr.CC(=O)c1c(F)cccc1F | O=C(CBr)c1c(F)cccc1F | null | null | C(C)OCC | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | 100 | [{"value": 100.0, "product": "BrCC(=O)C1=C(C=CC=C1F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 1-(2,6-difluorophenyl)ethanone (10.0 g) in diethyl ether (50 mL) was added anhydrous aluminum chloride (86 mg) and the mixture was stirred for 5 min. Bromine (3.3 mL) was added dropwise at 10-15° C. After stirring at room temperature for 2 hr, the mixture was poured into water, and the mixture was extr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | C(C)OCC | null | 0.083333 | BrBr.CC(=O)c1c(F)cccc1F>C(C)OCC>O=C(CBr)c1c(F)cccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-105a8ca46e104d9084d71d0ffe892f07 | CCOC(=O)CC#N.O=C(CBr)c1c(F)cccc1F>>CCOC(=O)C(C#N)CC(=O)c1c(F)cccc1F | C(#N)CC(=O)OCC.C(C)(C)N(CC)C(C)C.BrCC(=O)C1=C(C=CC=C1F)F>>C(#N)C(C(=O)OCC)CC(=O)C1=C(C=CC=C1F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]#[N:8].Br[CH2:9][C:10](=[O:11])[c:12]1[c:13]([F:14])[cH:15][cH:16][cH:17][c:18]1[F:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7]#[N:8])[CH2:9][C:10](=[O:11])[c:12]1[c:13]([F:14])[cH:15][cH:16][cH:17][c:18]1[F:19] | CCOC(=O)CC#N.O=C(CBr)c1c(F)cccc1F | CCOC(=O)C(C#N)CC(=O)c1c(F)cccc1F | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 8f6d4b304f760571a184e9fdd40a1eea1ac2caef68076ef062be84edd531cf09 | 4c05eab7fc11daae7c29afd57dcd00ee6caafc643a857cb0c2660dc4a28e52eb | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10]#[N;D1;H0:11]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:10]#[N;D1;H0:11])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | 81 | [{"value": 81.0, "product": "C(#N)C(C(=O)OCC)CC(=O)C1=C(C=CC=C1F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "C(#N)C(C(=O)OCC)CC(=O)C1=C(C=CC=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of ethyl cyanoacetate (7.24 g) and diisopropylethylamine (19.9 g) in tetrahydrofuran (30 mL) was added dropwise a solution of 2-bromo-1-(2,6-difluorophenyl)ethanone (15.16 g) in tetrahydrofuran (15 mL) at 10-15° C. The mixture was stirred at room temperature for 12 hr. The reaction mixture was filtered, a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester | Ketone.Ester | null | null | c1ccccc1 | HBr | O1CCCC1 | null | 12 | CCOC(=O)CC#N.O=C(CBr)c1c(F)cccc1F>O1CCCC1>CCOC(=O)C(C#N)CC(=O)c1c(F)cccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d84b5e71971e4e41b5b48b9f3f750528 | CCOC(=O)C(C#N)CC(=O)c1c(F)cccc1F.Cl>>CCOC(=O)c1cc(-c2c(F)cccc2F)[nH]c1Cl | C(#N)C(C(=O)OCC)CC(=O)C1=C(C=CC=C1F)F.C(C)(=O)OCC.Cl>>ClC=1NC(=CC1C(=O)OCC)C1=C(C=CC=C1F)F | O=[C:8]([CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18]#[N:17])[c:9]1[c:10]([F:11])[cH:12][cH:13][cH:14][c:15]1[F:16].[ClH:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[c:10]([F:11])[cH:12][cH:13][cH:14][c:15]2[F:16])[nH:17][c:18]1[Cl:19] | CCOC(=O)C(C#N)CC(=O)c1c(F)cccc1F.Cl | CCOC(=O)c1cc(-c2c(F)cccc2F)[nH]c1Cl | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | ee999686a7991e07d7c287a446be67936cb0259cc7da34bde8489e32aa619966 | 463beee1c06ff6990c2e1332d51dae761cf1d15bf3cb1e31ff2630a30ad5b435 | c1ccc(-c2ccc[nH]2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[CH;D3;+0:3](-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[c;H0;D3;+0:10](:[c:11](-[F;D1;H0:12]):[c:13]):[c:14](-[F;D1;H0:15]):[c:16].[ClH;D0;+0:17]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11](-[F;D1;H0:12]):... | 68 | [{"value": 68.0, "product": "ClC=1NC(=CC1C(=O)OCC)C1=C(C=CC=C1F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A solution (14 mL) of ethyl 2-cyano-4-(2,6-difluorophenyl)-4-oxobutanoate (13.83 g) in ethyl acetate was added dropwise to 4 mol/L hydrogen chloride-ethyl acetate solution (100 mL) at 10-15° C. The mixture was stirred at room temperature for 12 hr, and concentrated under reduced pressure. The residue was purified by si... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Aromatic halide.Ester | null | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | HO- | C(C)(=O)OCC | null | 12 | CCOC(=O)C(C#N)CC(=O)c1c(F)cccc1F.Cl>C(C)(=O)OCC>CCOC(=O)c1cc(-c2c(F)cccc2F)[nH]c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9bde0efe4776456b93ee9a0bc799c1cb | COC(=O)C(C#N)CC(=O)c1ccc(C2CCCCC2)cc1.Cl>>COC(=O)c1cc(-c2ccc(C3CCCCC3)cc2)[nH]c1Cl | C(#N)C(C(=O)OC)CC(=O)C1=CC=C(C=C1)C1CCCCC1.O1CCOCC1.Cl>>ClC=1NC(=CC1C(=O)OC)C1=CC=C(C=C1)C1CCCCC1 | O=[C:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[C:21]#[N:20])[c:8]1[cH:9][cH:10][c:11]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][cH:19]1.[ClH:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[nH:20][c:21]1[Cl:22... | COC(=O)C(C#N)CC(=O)c1ccc(C2CCCCC2)cc1.Cl | COC(=O)c1cc(-c2ccc(C3CCCCC3)cc2)[nH]c1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ee999686a7991e07d7c287a446be67936cb0259cc7da34bde8489e32aa619966 | 463beee1c06ff6990c2e1332d51dae761cf1d15bf3cb1e31ff2630a30ad5b435 | c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[CH;D3;+0:3](-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[ClH;D0;+0:15]>>[C;D1;H3:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[nH;D2;+0:... | null | [] | null | null | 8 | HOUR | 14% Hydrogen chloride-1,4-dioxane solution (50 mL) was added to methyl 2-cyano-4-(4-cyclohexylphenyl)-4-oxobutanoate (12.1 g) and the mixture was stirred at room temperature for 8 hr and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous ma... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Aromatic halide.Ester | null | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.C1CCCCC1 | HO- | null | null | 8 | COC(=O)C(C#N)CC(=O)c1ccc(C2CCCCC2)cc1.Cl>>COC(=O)c1cc(-c2ccc(C3CCCCC3)cc2)[nH]c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-519ff4b97d5e4f4da47a7cf86aa0eda5 | COC(=O)c1cc(-c2ccccc2)[nH]c1Cl>>COC(=O)c1c(Cl)[nH]c(-c2ccccc2)c1F | C(#N)CC(=O)OC.C(C(=O)C1=CC=CC=C1)Br.[O-]S(=O)(=O)C(F)(F)F.ClC1=[N+](C(=CC=C1)Cl)F.ClC=1NC(=CC1C(=O)OC)C1=CC=CC=C1>>ClC=1NC(=C(C1C(=O)OC)F)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([Cl:7])[nH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([Cl:7])[nH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]1[F:17] | COC(=O)c1cc(-c2ccccc2)[nH]c1Cl | COC(=O)c1c(Cl)[nH]c(-c2ccccc2)c1F | null | null | C(C)#N | Functional Group Addition | Aromatic fluorination | 4048bac0b4c21eb6e694a585c03c487c6380befb41bf01d9388a95029c960e33 | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccc(-c2ccc[nH]2)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[cH;D2;+0:6]:[c:7](-[c:8]):[#7;a:9]:[c:10]:1-[Cl;D1;H0:11]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:10](-[Cl;D1;H0:11]):[#7;a:9]:[c:7](-[c:8]):[c;H0;D3;+0:6]:1-[F;D1;H0:12] | 16.2 | [{"value": 16.0, "product": "ClC=1NC(=C(C1C(=O)OC)F)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.2, "product": "ClC=1NC(=C(C1C(=O)OC)F)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a suspension of methyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate (4.66 g) synthesized from methyl cyanoacetate and phenacyl bromide in the same manner as in Reference Example 95 and Reference Example 97 in acetonitrile (200 mL) was added 2,6-dichloro-N-fluoropyridinium triflate (6.26 g) over 10 min under ice-coolin... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | Other | C(C)#N | null | 2 | COC(=O)c1cc(-c2ccccc2)[nH]c1Cl>C(C)#N>COC(=O)c1c(Cl)[nH]c(-c2ccccc2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9131238d8acb4969be2a977c7e6f285c | COC(=O)CC#N.O=C(CBr)c1ccccc1>>COC(=O)C(C#N)CC(=O)c1ccccc1 | C(#N)CC(=O)OC.C(C)(C)N(CC)C(C)C.C(C(=O)C1=CC=CC=C1)Br>>C(#N)C(C(=O)OC)CC(=O)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]#[N:7].Br[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([C:6]#[N:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | COC(=O)CC#N.O=C(CBr)c1ccccc1 | COC(=O)C(C#N)CC(=O)c1ccccc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 8f6d4b304f760571a184e9fdd40a1eea1ac2caef68076ef062be84edd531cf09 | 4c05eab7fc11daae7c29afd57dcd00ee6caafc643a857cb0c2660dc4a28e52eb | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10]#[N;D1;H0:11]>>[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:10]#[N;D1;H0:11])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | 95 | [{"value": 95.0, "product": "C(#N)C(C(=O)OC)CC(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.6, "product": "C(#N)C(C(=O)OC)CC(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a suspension of methyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate (4.66 g) synthesized from methyl cyanoacetate and phenacyl bromide in the same manner as in Reference Example 95 and Reference Example 97 in acetonitrile (200 mL) was added 2,6-dichloro-N-fluoropyridinium triflate (6.26 g) over 10 min under ice-coolin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester | Ketone.Ester | null | null | c1ccccc1 | HBr | O1CCCC1 | null | 12 | COC(=O)CC#N.O=C(CBr)c1ccccc1>O1CCCC1>COC(=O)C(C#N)CC(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de13114bf9624623a4cbd95d7e9ba88d | CCOC(=O)C(C#N)CC(=O)c1c(F)cccc1F.Cl>>COC(=O)c1cc(-c2ccccc2)[nH]c1Cl | C(#N)C(C(=O)OCC)CC(=O)C1=C(C=CC=C1F)F.C(C)(=O)OCC.Cl>>ClC=1NC(=CC1C(=O)OC)C1=CC=CC=C1 | C[CH2:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][C:7](=O)[c:8]1[c:9](F)[cH:10][cH:11][cH:12][c:13]1F)[C:15]#[N:14].[ClH:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[nH:14][c:15]1[Cl:16] | CCOC(=O)C(C#N)CC(=O)c1c(F)cccc1F.Cl | COC(=O)c1cc(-c2ccccc2)[nH]c1Cl | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 35af3be39562adfa2ad324fe1de13666dad61852fa02459b726524c79d2f63a3 | e7bd1d55a47c3e143d871399746cf3601c5840f5b888f86bbeb382863a5d68d7 | c1ccc(-c2ccc[nH]2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7])-[CH2;D2;+0:8]-[C;H0;D3;+0:9](=O)-[c;H0;D3;+0:10]1:[c;H0;D3;+0:11](-F):[c:12]:[c:13]:[c:14]:[c;H0;D3;+0:15]:1-F.[ClH;D0;+0:16]>>[CH3;D1;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:10]2:[c... | 37 | [{"value": 37.0, "product": "ClC=1NC(=CC1C(=O)OC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a suspension of methyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate (4.66 g) synthesized from methyl cyanoacetate and phenacyl bromide in the same manner as in Reference Example 95 and Reference Example 97 in acetonitrile (200 mL) was added 2,6-dichloro-N-fluoropyridinium triflate (6.26 g) over 10 min under ice-coolin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ketone.Ester.Nitrile | Aromatic halide.Ester | c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | HF | C(C)(=O)OCC | null | 18 | CCOC(=O)C(C#N)CC(=O)c1c(F)cccc1F.Cl>C(C)(=O)OCC>COC(=O)c1cc(-c2ccccc2)[nH]c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-220ec73cbe7346479395b32bd15ef6e2 | CCOC(=O)c1cc(-c2c(F)cccc2F)[nH]c1Cl>>CCOC(=O)c1c[nH]c(-c2c(F)cccc2F)c1 | ClC=1NC(=CC1C(=O)OCC)C1=C(C=CC=C1F)F>>FC1=C(C(=CC=C1)F)C1=CC(=CN1)C(=O)OCC | Cl[c:7]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:18][c:9](-[c:10]2[c:11]([F:12])[cH:13][cH:14][cH:15][c:16]2[F:17])[nH:8]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9](-[c:10]2[c:11]([F:12])[cH:13][cH:14][cH:15][c:16]2[F:17])[cH:18]1 | CCOC(=O)c1cc(-c2c(F)cccc2F)[nH]c1Cl | CCOC(=O)c1c[nH]c(-c2c(F)cccc2F)c1 | null | [C].[Pd] | C(C)O | Functional Group Interconversion | Aromatic dehalogenation | 0ec084506a1195e403239281a55b47251adfd459417d17893b063b33c6f08040 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccc[nH]2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[cH;D2;+0:1]:1 | 44 | [{"value": 24.0, "product": "FC1=C(C(=CC=C1)F)C1=CC(=CN1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.0, "product": "FC1=C(C(=CC=C1)F)C1=CC(=CN1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 72 | HOUR | To a solution of ethyl 2-chloro-5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate (9.82 g) in ethanol (200 mL) was added 10% palladium carbon (50% containing water, 4.91 g), and the mixture was stirred under a hydrogen atmosphere at 40° C. for 72 hr. The reaction mixture was filtered, and the filtrate was concentrated un... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | Other | [C].[Pd].C(C)O | 40 | 72 | CCOC(=O)c1cc(-c2c(F)cccc2F)[nH]c1Cl>[C].[Pd].C(C)O>CCOC(=O)c1c[nH]c(-c2c(F)cccc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8d5160f7d2d428798d929bface03fd7 | COC(=O)c1cc(-c2ccc(C3CCCCC3)cc2)[nH]c1Cl>>COC(=O)c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | ClC=1NC(=CC1C(=O)OC)C1=CC=C(C=C1)C1CCCCC1.NC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C1CCCCC1>>C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)C(=O)OC | Cl[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:21][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[cH:19][cH:20]2)[nH:7]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[cH:19][cH:20]2)[cH:21]1 | COC(=O)c1cc(-c2ccc(C3CCCCC3)cc2)[nH]c1Cl | COC(=O)c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | null | [C].[Pd] | CO.C(C)(=O)OCC | Functional Group Interconversion | Aromatic dehalogenation | 0ec084506a1195e403239281a55b47251adfd459417d17893b063b33c6f08040 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9]>>[C;D1;H3:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[cH;D2;+0:1]:1 | 41.1 | [{"value": 41.0, "product": "C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.1, "product": "C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 14 | HOUR | To a solution of a nearly 1:1 mixture (3.41 g) of methyl 2-chloro-5-(4-cyclohexylphenyl)-1H-pyrrole-3-carboxylate and methyl 2-amino-5-(4-cyclohexylphenyl)-3-furoate in methanol (30 mL) and ethyl acetate (10 mL) was added 10% palladium carbon (50% containing water, 0.34 g), and the mixture was stirred under a hydrogen ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.C1CCCCC1 | Other | [C].[Pd].CO.C(C)(=O)OCC | 50 | 14 | COC(=O)c1cc(-c2ccc(C3CCCCC3)cc2)[nH]c1Cl>[C].[Pd].CO.C(C)(=O)OCC>COC(=O)c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1d1310ec7044f80b7e27927a463a9dd | COC(=O)c1c(Cl)[nH]c(-c2ccccc2)c1F>>COC(=O)c1c[nH]c(-c2ccccc2)c1F | ClC=1NC(=C(C1C(=O)OC)F)C1=CC=CC=C1.C(C)N(CC)CC>>FC=1C(=CNC1C1=CC=CC=C1)C(=O)OC | Cl[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:15]([F:16])[c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[nH:7]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]1[F:16] | COC(=O)c1c(Cl)[nH]c(-c2ccccc2)c1F | COC(=O)c1c[nH]c(-c2ccccc2)c1F | null | [C].[Pd] | CO | Functional Group Interconversion | Aromatic dehalogenation | 0ec084506a1195e403239281a55b47251adfd459417d17893b063b33c6f08040 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccc[nH]2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9]>>[C;D1;H3:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[cH;D2;+0:1]:1 | 86,784.9 | [{"value": 87.0, "product": "FC=1C(=CNC1C1=CC=CC=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86784.9, "product": "FC=1C(=CNC1C1=CC=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Methyl 2-chloro-4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate (0.92 mg), 10% palladium carbon (50% containing water, 0.20 g) and triethylamine (0.56 mL) were suspended in methanol (30 mL), and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 hr. The reaction mixture was filtered through celite... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | Other | [C].[Pd].CO | null | 2 | COC(=O)c1c(Cl)[nH]c(-c2ccccc2)c1F>[C].[Pd].CO>COC(=O)c1c[nH]c(-c2ccccc2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b7ea2b2ed80244d19dc07e792bbb284a | CCOC(=O)c1c[nH]c(-c2c(F)cccc2F)c1>>OCc1c[nH]c(-c2c(F)cccc2F)c1 | O.[H-].C(C(C)C)[Al+]CC(C)C.FC1=C(C(=CC=C1)F)C1=CC(=CN1)C(=O)OCC>>FC1=C(C(=CC=C1)F)C1=CC(=CN1)CO | CCO[C:2](=[O:1])[c:3]1[cH:4][nH:5][c:6](-[c:7]2[c:8]([F:9])[cH:10][cH:11][cH:12][c:13]2[F:14])[cH:15]1>>[OH:1][CH2:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[c:8]([F:9])[cH:10][cH:11][cH:12][c:13]2[F:14])[cH:15]1 | CCOC(=O)c1c[nH]c(-c2c(F)cccc2F)c1 | OCc1c[nH]c(-c2c(F)cccc2F)c1 | null | null | O1CCCC1.C1(=CC=CC=C1)C.C(C)(=O)OCC.S(=O)(=O)([O-])[O-].[Mg+2] | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2ccc[nH]2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 97 | [{"value": 97.0, "product": "FC1=C(C(=CC=C1)F)C1=CC(=CN1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "FC1=C(C(=CC=C1)F)C1=CC(=CN1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution (35 mL) of ethyl 5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate (3.35 g) in tetrahydrofuran was cooled to −50° C., and a 1.5 mol/L solution (30 mL) of diisobutylaluminum hydride in toluene was added dropwise by small portions. The mixture was stirred at the same temperature for 1 hr, water was added to the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cc[nH]c1.c1ccccc1 | HO- | O1CCCC1.C1(=CC=CC=C1)C.C(C)(=O)OCC.S(=O)(=O)([O-])[O-].[Mg+2] | null | 1 | CCOC(=O)c1c[nH]c(-c2c(F)cccc2F)c1>O1CCCC1.C1(=CC=CC=C1)C.C(C)(=O)OCC.S(=O)(=O)([O-])[O-].[Mg+2]>OCc1c[nH]c(-c2c(F)cccc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec06b0df98f54598b2ba320b02085040 | COC(=O)c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1>>OCc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | Cl.C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)C(=O)OC.[H-].C(C(C)C)[Al+]CC(C)C>>C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)CO | CO[C:2](=[O:1])[c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18]2)[cH:19]1>>[OH:1][CH2:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18]2)[cH:19]1 | COC(=O)c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | OCc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | null | null | O1CCCC1.C1(=CC=CC=C1)C.C(C)(=O)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 40 | [{"value": 40.0, "product": "C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.6, "product": "C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of methyl 5-(4-cyclohexylphenyl)-1H-pyrrole-3-carboxylate (3.0 g) in absolute tetrahydrofuran (40 mL) was added dropwise a 1.5 mol/L solution (21.0 mL) of diisobutylaluminum hydride in toluene at −78° C. The mixture was further stirred at the same temperature for 2 hr. To the reaction mixture was added 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cc[nH]c1.c1ccccc1.C1CCCCC1 | Other | O1CCCC1.C1(=CC=CC=C1)C.C(C)(=O)OCC | null | 2 | COC(=O)c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1>O1CCCC1.C1(=CC=CC=C1)C.C(C)(=O)OCC>OCc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6978548cbfd141b799db12b575d852a6 | OCc1c[nH]c(-c2c(F)cccc2F)c1>>O=Cc1c[nH]c(-c2c(F)cccc2F)c1 | FC1=C(C(=CC=C1)F)C1=CC(=CN1)CO.C[N+]1(CCOCC1)[O-]>>FC1=C(C(=CC=C1)F)C1=CC(=CN1)C=O | [OH:1][CH2:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[c:8]([F:9])[cH:10][cH:11][cH:12][c:13]2[F:14])[cH:15]1>>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[c:8]([F:9])[cH:10][cH:11][cH:12][c:13]2[F:14])[cH:15]1 | OCc1c[nH]c(-c2c(F)cccc2F)c1 | O=Cc1c[nH]c(-c2c(F)cccc2F)c1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | C(C)#N.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-c2ccc[nH]2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 77 | [{"value": 77.0, "product": "FC1=C(C(=CC=C1)F)C1=CC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.5, "product": "FC1=C(C(=CC=C1)F)C1=CC(=CN1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution (26 mL) of [5-(2,6-difluorophenyl)-1H-pyrrol-3-yl]methanol (2.56 g) in acetonitrile were added tetra-n-propylammonium perruthenate (430 mg), N-methylmorpholine N-oxide (2.15 g) and molecular sieves 4A powder (5 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cc[nH]c1.c1ccccc1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(C)#N.C(C)(=O)OCC | null | 2 | OCc1c[nH]c(-c2c(F)cccc2F)c1>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(C)#N.C(C)(=O)OCC>O=Cc1c[nH]c(-c2c(F)cccc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-163ff17ba8694624aa224fffbda041ae | OCc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1>>O=Cc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)CO.C[N+]1(CCOCC1)[O-]>>C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)C=O | [OH:1][CH2:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18]2)[cH:19]1>>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18]2)[cH:19]1 | OCc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | O=Cc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | C(C)#N.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 53.4 | [{"value": 53.0, "product": "C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.4, "product": "C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution (35 mL) of [5-(4-cyclohexylphenyl)-1H-pyrrol-3-yl]methanol (1.00 g) in acetonitrile were added tetra-n-propylammonium perruthenate (115 mg), N-methylmorpholine N-oxide (0.60 g) and molecular sieves 4A powder (1.15 g) under ice-cooling. The mixture was stirred at room temperature for 1.5 hr, and the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cc[nH]c1.c1ccccc1.C1CCCCC1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(C)#N.C(C)(=O)OCC | null | 1.5 | OCc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(C)#N.C(C)(=O)OCC>O=Cc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-313288ee16684b83b555dbcdd7c52e28 | Cc1ccccc1Br.O=C(O)C(F)(F)Cl>>Cc1ccccc1C(=O)C(F)(F)Cl | ClC(C(=O)O)(F)F.[Mg].II.BrC1=C(C=CC=C1)C.[Cl-].[NH4+]>>ClC(C(=O)C1=C(C=CC=C1)C)(F)F | Br[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1.O[C:8](=[O:9])[C:10]([F:11])([F:12])[Cl:13]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[C:10]([F:11])([F:12])[Cl:13] | Cc1ccccc1Br.O=C(O)C(F)(F)Cl | Cc1ccccc1C(=O)C(F)(F)Cl | null | null | C(C)OCC | C-C Coupling | OtherReaction | a68697290bfa0dc1acf39da3d62d1964bdd31d9378f6c352a4a6c9727596388a | e8d827fd3c4c9e4f506ca0217eb2834296a2d5d73d1289088c88acc955f13a34 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[Cl;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[Cl;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12]):[c:2]:[c:3] | 31.2 | [{"value": 31.0, "product": "ClC(C(=O)C1=C(C=CC=C1)C)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.2, "product": "ClC(C(=O)C1=C(C=CC=C1)C)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Magnesium (flake, 6.2 g) was suspended in diethyl ether (10 mL), and iodine (small amount) was added and a solution of 2-bromotoluene (43.26 g) in diethyl ether (100 mL) were slowly added dropwise. After stirring at room temperature for 1 hr, the reaction mixture was added dropwise to a solution of chlorodifluoroacetic... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)OCC | null | 1 | Cc1ccccc1Br.O=C(O)C(F)(F)Cl>C(C)OCC>Cc1ccccc1C(=O)C(F)(F)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-458204c058a546459660b75e02c2c7f6 | Cc1ccccc1C(=O)C(F)(F)Cl.II>>Cc1ccccc1C(=O)C(F)(F)I | O.C[Si](C)(C)Cl.ClC(C(=O)C1=C(C=CC=C1)C)(F)F.II>>FC(C(=O)C1=C(C=CC=C1)C)(I)F | Cl[C:10]([C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)=[O:9])([F:11])[F:12].I[I:13]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[C:10]([F:11])([F:12])[I:13] | Cc1ccccc1C(=O)C(F)(F)Cl.II | Cc1ccccc1C(=O)C(F)(F)I | null | [Zn] | C(C)#N | Functional Group Interconversion | OtherReaction | 108cc7e043ac402fc9d1d41618d4709c8e5568ce46d961ad76a93e068c18eb94 | 282cb34e22ed9b87e08e917842a62c2e5c4daf28c7f2abf97c332671d1cb6f2d | c1ccccc1 | Cl-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6].I-[I;H0;D1;+0:7]>>[F;D1;H0:2]-[C;H0;D4;+0:1](-[F;D1;H0:3])(-[I;H0;D1;+0:7])-[C:4](=[O;D1;H0:5])-[c:6] | 63.7 | [{"value": 46.0, "product": "FC(C(=O)C1=C(C=CC=C1)C)(I)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.7, "product": "FC(C(=O)C1=C(C=CC=C1)C)(I)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 3 | HOUR | To a suspension of zinc (1.6 g) in acetonitrile (40 mL) were added trimethylsilyl chloride (3.1 mL) and 2-chloro-2,2-difluoro-1-(2-methylphenyl)ethanone (4.0 g), and the mixture was stirred at 55° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, iodine (3.5 g) was added, and the mixture was fu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Ketone | Tertiary halide.Tertiary halide.Tertiary halide | null | null | c1ccccc1 | I- | [Zn].C(C)#N | 55 | 3 | Cc1ccccc1C(=O)C(F)(F)Cl.II>[Zn].C(C)#N>Cc1ccccc1C(=O)C(F)(F)I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f899931ab9814f09824145497ed8f6a0 | Cc1ccccc1C(=O)C(F)(F)CC(I)[Si](C)(C)C.N>>Cc1ccccc1-c1[nH]ccc1F | FC(C(=O)C1=C(C=CC=C1)C)(CC([Si](C)(C)C)I)F.N>>FC1=C(NC=C1)C1=C(C=CC=C1)C | C[Si](C)(C)[CH:10](I)[CH2:11][C:12](F)([C:8](=O)[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)[F:13].[NH3:9]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[nH:9][cH:10][cH:11][c:12]1[F:13] | Cc1ccccc1C(=O)C(F)(F)CC(I)[Si](C)(C)C.N | Cc1ccccc1-c1[nH]ccc1F | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 051cdeb87a7dd311937642c85ee3e8d64053c8d8e9e6f70675fc2d89bcd71b45 | 0282117e50c66ba8a00fb17e01dc7e1944ddf267d0e68532e263d5fd206fd73f | c1ccc(-c2ccc[nH]2)cc1 | C-[Si](-C)(-C)-[CH;D3;+0:1](-I)-[CH2;D2;+0:2]-[C;H0;D4;+0:3](-F)(-[F;D1;H0:4])-[C;H0;D3;+0:5](=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C;D1;H3:10]):[c:11].[NH3;D0;+0:12]>>[C;D1;H3:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[nH;D2;+0:12]:[cH;D2;+0:1]:[cH;D2;+0:2]:[c;H0;D3;+0:3]:1-[F;D1;H0:4]):[c:7]:[c:8] | 78 | [{"value": 78.0, "product": "FC1=C(NC=C1)C1=C(C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution (20 mL) of 2,2-difluoro-4-iodo-1-(2-methylphenyl)-4-trimethylsilylbutan-1-one (2.5 g) in tetrahydrofuran was added 28% aqueous ammonia solution (6 mL) and the mixture was stirred at room temperature for 14 hr. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated bri... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Secondary halide.Ketone.Silyl protective group | Aromatic halide | null | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | HF.I- | O1CCCC1 | null | 14 | Cc1ccccc1C(=O)C(F)(F)CC(I)[Si](C)(C)C.N>O1CCCC1>Cc1ccccc1-c1[nH]ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df583e9269374d3c985cdf6acd20a7a8 | Cc1ccccc1B(O)O.O=Cc1c[nH]c(Br)c1>>Cc1ccccc1-c1cc(C=O)c[nH]1 | COCCOC.BrC1=CC(=CN1)C=O.CC1=C(C=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>CC1=C(C=CC=C1)C1=CC(=CN1)C=O | OB(O)[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1.Br[c:8]1[cH:9][c:10]([CH:11]=[O:12])[cH:13][nH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]([CH:11]=[O:12])[cH:13][nH:14]1 | Cc1ccccc1B(O)O.O=Cc1c[nH]c(Br)c1 | Cc1ccccc1-c1cc(C=O)c[nH]1 | null | null | O | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc[nH]2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[C;D1;H3:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1):[c:9]:[c:10] | 68 | [{"value": 68.0, "product": "CC1=C(C=CC=C1)C1=CC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.6, "product": "CC1=C(C=CC=C1)C1=CC(=CN1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | null | null | 5-Bromo-1H-pyrrole-3-carbaldehyde (100 mg), 2-methylphenylboronic acid (94 mg) and sodium carbonate (146 mg) were suspended in a mixed solvent of 1,2-dimethoxyethane (5 mL) and water (2 mL), and the mixture was sufficiently degassed under a nitrogen atmosphere. Tetrakis(triphenylphosphine)palladium (33 mg) was added, a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | HBr.B | O | 105 | null | Cc1ccccc1B(O)O.O=Cc1c[nH]c(Br)c1>O>Cc1ccccc1-c1cc(C=O)c[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a49aea07a2da49c7b258ba354c83128c | O=C1CCC(=O)N1Cl.O=Cc1c[nH]c(-c2ccccc2F)c1>>O=Cc1c[nH]c(-c2ccccc2F)c1Cl | O.FC1=C(C=CC=C1)C1=CC(=CN1)C=O.ClN1C(CCC1=O)=O>>ClC=1C(=CNC1C1=C(C=CC=C1)F)C=O | O=C1CCC(=O)N1[Cl:15].[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[F:13])[cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[F:13])[c:14]1[Cl:15] | O=C1CCC(=O)N1Cl.O=Cc1c[nH]c(-c2ccccc2F)c1 | O=Cc1c[nH]c(-c2ccccc2F)c1Cl | null | null | CN(C=O)C | Functional Group Interconversion | Chlorination | 40ba41cd9c6955f8bb4a47b285f327e8347ac41f3539d665e8b27d9300f356ae | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(-c2ccc[nH]2)cc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4]1:[c:5]:[#7;a:6]:[c:7](-[c:8]):[cH;D2;+0:9]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[c:4](-[C:3]=[O;D1;H0:2]):[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 46.5 | [{"value": 46.0, "product": "ClC=1C(=CNC1C1=C(C=CC=C1)F)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.5, "product": "ClC=1C(=CNC1C1=C(C=CC=C1)F)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | To a solution (15 mL) of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (1.0 g) in N,N-dimethylformamide was added N-chlorosuccinimide (0.71 g) at 0° C., and the mixture was stirred at 60° C. for 2 hr. The mixture was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate. The extrac... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | HO- | CN(C=O)C | 60 | 2 | O=C1CCC(=O)N1Cl.O=Cc1c[nH]c(-c2ccccc2F)c1>CN(C=O)C>O=Cc1c[nH]c(-c2ccccc2F)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e83aa001928401983a83acc4bd6dd91 | O=Cc1c[nH]c(-c2ccccc2F)c1>>O=Cc1c[nH]c(-c2ccccc2F)c1F | C(O)([O-])=O.[Na+].FC1=C(C=CC=C1)C1=CC(=CN1)C=O.[O-]S(=O)(=O)C(F)(F)F.ClC1=[N+](C(=CC=C1)Cl)F>>FC=1C(=CNC1C1=C(C=CC=C1)F)C=O | [O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[F:13])[cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[F:13])[c:14]1[F:15] | O=Cc1c[nH]c(-c2ccccc2F)c1 | O=Cc1c[nH]c(-c2ccccc2F)c1F | null | null | O1CCCC1 | Functional Group Addition | Aromatic fluorination | 4048bac0b4c21eb6e694a585c03c487c6380befb41bf01d9388a95029c960e33 | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccc(-c2ccc[nH]2)cc1 | [O;D1;H0:1]=[C:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6](-[c:7]):[cH;D2;+0:8]:1>>[F;D1;H0:9]-[c;H0;D3;+0:8]1:[c:3](-[C:2]=[O;D1;H0:1]):[c:4]:[#7;a:5]:[c:6]:1-[c:7] | 13 | [{"value": 13.0, "product": "FC=1C(=CNC1C1=C(C=CC=C1)F)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.7, "product": "FC=1C(=CNC1C1=C(C=CC=C1)F)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution (60 mL) of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (3.1 g) in tetrahydrofuran was added 2,6-dichloro-N-fluoropyridinium triflate (5.6 g) at 0° C., and the mixture was stirred at the same temperature for 2 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and t... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | Other | O1CCCC1 | null | 2 | O=Cc1c[nH]c(-c2ccccc2F)c1>O1CCCC1>O=Cc1c[nH]c(-c2ccccc2F)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88d492a5e242401fbc7ef19574437c3b | O=[N+]([O-])O.Oc1ncccc1C(F)(F)F>>O=[N+]([O-])c1cnc(O)c(C(F)(F)F)c1 | OC1=NC=CC=C1C(F)(F)F.S(O)(O)(=O)=O.[N+](=O)(O)[O-]>>[N+](=O)([O-])C=1C=C(C(=NC1)O)C(F)(F)F | O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][n:6][c:7]([OH:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]([OH:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | O=[N+]([O-])O.Oc1ncccc1C(F)(F)F | O=[N+]([O-])c1cnc(O)c(C(F)(F)F)c1 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | cb3ba0bb7f4ff246f608a5c967bfb512792a47826af0eb60d49c2f2aea6e8ead | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccncc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#7;a:4]1:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:[c:9]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:4]:[c:5]:1 | 69 | [{"value": 69.0, "product": "[N+](=O)([O-])C=1C=C(C(=NC1)O)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 5 | MINUTE | 2-Hydroxy-3-(trifluoromethyl)pyridine (3.0 g) was added to conc. sulfuric acid (18 mL) under ice-cooling, and the mixture was stirred at the same temperature for 5 min. Fuming nitric acid (90-95%, 7 mL) was added dropwise over 5 min, and the mixture was allowed to return to room temperature over 2 hr, heated to 50° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | null | 50 | 0.083333 | O=[N+]([O-])O.Oc1ncccc1C(F)(F)F>>O=[N+]([O-])c1cnc(O)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4652682c7d4a4d75a1ee469f5d8fd15d | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc(O)c(C(F)(F)F)c1>>O=[N+]([O-])c1cnc(Cl)c(C(F)(F)F)c1 | [N+](=O)([O-])C=1C=C(C(=NC1)O)C(F)(F)F.P(Cl)(Cl)(Cl)(Cl)Cl.P(=O)(Cl)(Cl)Cl>>ClC1=NC=C(C=C1C(F)(F)F)[N+](=O)[O-] | O=P(Cl)(Cl)[Cl:8].O[c:7]1[n:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:14][c:9]1[C:10]([F:11])([F:12])[F:13]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]([Cl:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc(O)c(C(F)(F)F)c1 | O=[N+]([O-])c1cnc(Cl)c(C(F)(F)F)c1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | ab85b19a1f19bdb0596b983dc6471067aedf5e7b894e737e6d16cd077bd81b42 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccncc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]):[c:10]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]):[c:10] | 77 | [{"value": 77.0, "product": "ClC1=NC=C(C=C1C(F)(F)F)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.6, "product": "ClC1=NC=C(C=C1C(F)(F)F)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 3 | HOUR | A mixture of 5-nitro-3-(trifluoromethyl)pyridin-2-ol (2.65 g), phosphorus pentachloride (3.17 g) and phosphorus oxychloride (1.5 mL) was stirred at 90° C. for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice, and the mixture was extracted with ethyl acetate. The extract was washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | null | 90 | 3 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc(O)c(C(F)(F)F)c1>>O=[N+]([O-])c1cnc(Cl)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-83e3531e09504611a6037eefb446e02f | O=[N+]([O-])c1cnc(Cl)c(C(F)(F)F)c1>>Nc1cnc(Cl)c(C(F)(F)F)c1 | [Cl-].[NH4+].O.ClC1=NC=C(C=C1C(F)(F)F)[N+](=O)[O-]>>ClC1=C(C=C(C=N1)N)C(F)(F)F | O=[N+:1]([O-])[c:2]1[cH:3][n:4][c:5]([Cl:6])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1>>[NH2:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1 | O=[N+]([O-])c1cnc(Cl)c(C(F)(F)F)c1 | Nc1cnc(Cl)c(C(F)(F)F)c1 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccncc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 65 | [{"value": 65.0, "product": "ClC1=C(C=C(C=N1)N)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "ClC1=C(C=C(C=N1)N)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Reduced iron (1.3 g) and ammonium chloride (2.1 g) were added to water (40 mL), and the mixture was stirred at room temperature for 5 min. A solution of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (1.8 g) in methanol (40 mL) was added, and the mixture was stirred at room temperature for 1 hr. Reduced iron (2.3 g) was ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1 | Other | CO | null | 0.083333 | O=[N+]([O-])c1cnc(Cl)c(C(F)(F)F)c1>CO>Nc1cnc(Cl)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fd4e953545234f1ca82bae093906a7d8 | Cl.Nc1cnc(Cl)c(C(F)(F)F)c1.O=S=O>>O=S(=O)(Cl)c1cnc(Cl)c(C(F)(F)F)c1 | S(=O)=O.N(=O)[O-].[Na+].ClC1=C(C=C(C=N1)N)C(F)(F)F.Cl.Cl>>ClC1=C(C=C(C=N1)S(=O)(=O)Cl)C(F)(F)F | [ClH:4].N[c:5]1[cH:6][n:7][c:8]([Cl:9])[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1.[O:1]=[S:2]=[O:3]>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][n:7][c:8]([Cl:9])[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1 | Cl.Nc1cnc(Cl)c(C(F)(F)F)c1.O=S=O | O=S(=O)(Cl)c1cnc(Cl)c(C(F)(F)F)c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | d44a4364e5511e440a48fb914cbd59017338faff430f0e7127e14fae8b0eff0a | 49dcc8f7b4471977f8fe724b4dd774612c303d853f75a373d5b25cc7ccd4c205 | c1ccncc1 | N-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[ClH;D0;+0:7].[O;D1;H0:8]=[S;H0;D2;+0:9]=[O;D1;H0:10]>>[Cl;H0;D1;+0:7]-[S;H0;D4;+0:9](=[O;D1;H0:8])(=[O;D1;H0:10])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 27 | [{"value": 27.0, "product": "ClC1=C(C=C(C=N1)S(=O)(=O)Cl)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice-cooling, thionyl chloride (4 mL) was added dropwise over 20 min to water (27 mL). The mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, 6-chloro-5-(trifluoromethyl)pyridine-3-amine (1.14 g) was added to concentrated hydrochloric acid (9 mL) with stirri... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonyl halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | O | null | null | Cl.Nc1cnc(Cl)c(C(F)(F)F)c1.O=S=O>O>O=S(=O)(Cl)c1cnc(Cl)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8124e260b99f48bdb6170f7787b35dd9 | Cc1nc(Cl)ccc1N.Cl.O=S=O>>Cc1nc(Cl)ccc1S(=O)(=O)Cl | S(=O)=O.N(=O)[O-].[Na+].Cl.NC=1C=CC(=NC1C)Cl>>ClC1=CC=C(C(=N1)C)S(=O)(=O)Cl | N[c:8]1[c:2]([CH3:1])[n:3][c:4]([Cl:5])[cH:6][cH:7]1.[ClH:12].[S:9](=[O:10])=[O:11]>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[S:9](=[O:10])(=[O:11])[Cl:12] | Cc1nc(Cl)ccc1N.Cl.O=S=O | Cc1nc(Cl)ccc1S(=O)(=O)Cl | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | d44a4364e5511e440a48fb914cbd59017338faff430f0e7127e14fae8b0eff0a | 49dcc8f7b4471977f8fe724b4dd774612c303d853f75a373d5b25cc7ccd4c205 | c1ccncc1 | N-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].[ClH;D0;+0:8].[O;D1;H0:9]=[S;H0;D2;+0:10]=[O;D1;H0:11]>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[S;H0;D4;+0:10](-[Cl;H0;D1;+0:8])(=[O;D1;H0:9])=[O;D1;H0:11] | 67 | [{"value": 67.0, "product": "ClC1=CC=C(C(=N1)C)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under ice-cooling, thionyl chloride (4 mL) was added dropwise to water (24 mL) over 20 min. The mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, to the concentrated hydrochloric acid (6 mL) was added 5-amino-2-chloro-6-methylpyridine (1.0 g) with stirring under... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonyl halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | O | null | null | Cc1nc(Cl)ccc1N.Cl.O=S=O>O>Cc1nc(Cl)ccc1S(=O)(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24fc362e9e4f48f08ac10fb8dd7b4243 | COC(=O)c1c[nH]c(-c2ccccc2)c1F.O=S(=O)(Cl)c1cccnc1>>COC(=O)c1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F | Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.C1COCCOCCOCCOCCO1.FC=1C(=CNC1C1=CC=CC=C1)C(=O)OC.[H-].[Na+]>>FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24]1[F:25].Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21... | COC(=O)c1c[nH]c(-c2ccccc2)c1F.O=S(=O)(Cl)c1cccnc1 | COC(=O)c1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F | null | null | O1CCCC1.O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14](-[c:15]):[nH;D2;+0:16]:[c:17]:1>>[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14](-[c:15]):[n;H0;D3;+0:16](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])... | 73 | [{"value": 73.0, "product": "FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.9, "product": "FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | By a similar reaction as in Reference Example 36 and using methyl 4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate (172 mg), the title compound was obtained as a colorless solid (yield 206 mg, 73%). More specifically, to a solution of methyl 4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate (172 mg) in tetrahydrofuran (10 mL) was a... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1.c1ccccc1 | HCl | O1CCCC1.O | null | 0.25 | COC(=O)c1c[nH]c(-c2ccccc2)c1F.O=S(=O)(Cl)c1cccnc1>O1CCCC1.O>COC(=O)c1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-45007b94ab8d42eabd48f68260c7a547 | COC(=O)c1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F>>O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F | O.[H-].C(C(C)C)[Al+]CC(C)C.FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C(=O)OC.C(C)(=O)OCC>>FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C=O | CO[C:2](=[O:1])[c:3]1[cH:4][n:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1[F:23]>>[O:1]=[CH:2][c:3]1[cH:4][n:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1[F:23... | COC(=O)c1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F | O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F | null | null | O1CCCC1.C1(=CC=CC=C1)C | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[#16:7]):[c:8]:1>>[#16:7]-[#7;a:6]1:[c:5]:[c:4]:[c:3](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:8]:1 | 67.1 | [{"value": 67.0, "product": "FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.1, "product": "FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Under a nitrogen atmosphere, a solution of methyl 4-fluoro-5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carboxylate (200 mg) in tetrahydrofuran (10 mL) was cooled to −78° C., and a 1.5 mol/L solution (1.85 mL) of diisobutylaluminum hydride in toluene was added with stirring. After stirring at the same temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1cc[nH]c1.c1ccncc1.c1ccccc1 | HO- | O1CCCC1.C1(=CC=CC=C1)C | 0 | null | COC(=O)c1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F>O1CCCC1.C1(=CC=CC=C1)C>O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79e4e84da2e64437811dc45c52d3b3eb | O=Cc1c[nH]c(-c2c(F)cccc2F)c1.O=S(=O)(Cl)c1cccnc1>>O=Cc1cc(-c2c(F)cccc2F)n(S(=O)(=O)c2cccnc2)c1 | Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.C1COCCOCCOCCOCCO1.FC1=C(C(=CC=C1)F)C1=CC(=CN1)C=O.[H-].[Na+]>>FC1=C(C(=CC=C1)F)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[c:7]([F:8])[cH:9][cH:10][cH:11][c:12]2[F:13])[nH:14][cH:24]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[c:7]([F:8])[cH:9][cH:10][cH:11][c:12]2[F:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH... | O=Cc1c[nH]c(-c2c(F)cccc2F)c1.O=S(=O)(Cl)c1cccnc1 | O=Cc1cc(-c2c(F)cccc2F)n(S(=O)(=O)c2cccnc2)c1 | null | null | O1CCCC1.[Cl-].[Na+].O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:13]1:[c:12]:[c:11](-[C:10]=[O;D1;H0:9]):[c:16]:[c:14]:1-[c:15] | 84 | [{"value": 84.0, "product": "FC1=C(C(=CC=C1)F)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "FC1=C(C(=CC=C1)F)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 5-(2,6-difluorophenyl)-1H-pyrrole-3-carbaldehyde (420 mg) in tetrahydrofuran (42 mL) was added sodium hydride (60% in oil, 244 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (1.34 g) was added dropwise and the mixture was stirred for 30 min. 3-Pyridylsulfonyl chloride hydroc... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1.[Cl-].[Na+].O | null | 0.5 | O=Cc1c[nH]c(-c2c(F)cccc2F)c1.O=S(=O)(Cl)c1cccnc1>O1CCCC1.[Cl-].[Na+].O>O=Cc1cc(-c2c(F)cccc2F)n(S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e50b74befd8425a8fb7dd35a1328ccc | O=Cc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1.O=S(=O)(Cl)c1cccnc1>>O=Cc1cc(-c2ccc(C3CCCCC3)cc2)n(S(=O)(=O)c2cccnc2)c1 | [H-].[Na+].C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1)C=O.N1=CC(=CC=C1)S(=O)(=O)Cl>>C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17]2)[nH:18][cH:28]1.Cl[S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][cH:25][n:26][cH:27]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][... | O=Cc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1.O=S(=O)(Cl)c1cccnc1 | O=Cc1cc(-c2ccc(C3CCCCC3)cc2)n(S(=O)(=O)c2cccnc2)c1 | null | null | O1CCCC1 | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccc(C2CCCCC2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[n;H0;D3;+0:13](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]):[c:14](-[c:15]):[c:16]:1 | 98.2 | [{"value": 97.0, "product": "C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.2, "product": "C1(CCCCC1)C1=CC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Sodium hydride (60% in oil, 68 mg) was added to a solution of 5-(4-cyclohexylphenyl)-1H-pyrrole-3-carbaldehyde (0.17 g) in tetrahydrofuran (12 mL) at room temperature. The mixture was stirred for 20 min, 3-pyridinesulfonyl chloride (0.19 g) was added, and the mixture was stirred at room temperature for 3 hr. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.C1CCCCC1.c1ccncc1 | HCl | O1CCCC1 | null | 0.333333 | O=Cc1c[nH]c(-c2ccc(C3CCCCC3)cc2)c1.O=S(=O)(Cl)c1cccnc1>O1CCCC1>O=Cc1cc(-c2ccc(C3CCCCC3)cc2)n(S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9c6dc74a8624dce83e08f84ae62bccf | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1ccc(Cl)nc1>>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccc(Cl)nc2)c1 | FC1=C(C=CC=C1)C1=CC(=CN1)C=O.ClC1=CC=C(C=N1)S(=O)(=O)Cl>>ClC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=C(C=CC=C1)F)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[nH:13][cH:24]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[n:22][cH:23]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][c:20]([Cl:21])[n:22][... | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1ccc(Cl)nc1 | O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccc(Cl)nc2)c1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:13]1:[c:12]:[c:11](-[C:10]=[O;D1;H0:9]):[c:16]:[c:14]:1-[c:15] | 66 | [{"value": 66.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar reaction as in Reference Example 65 and using 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (893 mg) and 6-chloropyridine-3-sulfonyl chloride (1.30 g), the title compound was obtained as a pale-red solid (yield 1.14 g, 66%). More specifically, 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (893 mg) was dissol... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | null | null | null | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1ccc(Cl)nc1>>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccc(Cl)nc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18e1e79248804e76927271685b61fe9c | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1ccc(Cl)nc1>>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccc(Cl)nc2)c1 | ClC1=CC=C(C=N1)S(=O)(=O)Cl.[H-].[Na+].FC1=C(C=CC=C1)C1=CC(=CN1)C=O.C1COCCOCCOCCOCCO1>>ClC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=C(C=CC=C1)F)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[nH:13][cH:24]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[n:22][cH:23]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][c:20]([Cl:21])[n:22][... | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1ccc(Cl)nc1 | O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccc(Cl)nc2)c1 | null | null | O1CCCC1.O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:13]1:[c:12]:[c:11](-[C:10]=[O;D1;H0:9]):[c:16]:[c:14]:1-[c:15] | 66.2 | [{"value": 66.0, "product": "ClC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=C(C=CC=C1)F)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "ClC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=C(C=CC=C1)F)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | By a similar reaction as in Reference Example 65 and using 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (893 mg) and 6-chloropyridine-3-sulfonyl chloride (1.30 g), the title compound was obtained as a pale-red solid (yield 1.14 g, 66%). More specifically, 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (893 mg) was dissol... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1.O | null | 0.25 | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1ccc(Cl)nc1>O1CCCC1.O>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccc(Cl)nc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25fb8434bdeb463e91b2ef83263f66cc | CB(O)O.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccc(Cl)nc2)c1>>Cc1ccc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2F)cn1 | C(O)([O-])=O.[Na+].ClC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=C(C=CC=C1)F)C=O.CB(O)O.C([O-])([O-])=O.[K+].[K+]>>FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)C=O | OB(O)[CH3:1].Cl[c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11]([CH:12]=[O:13])[cH:14][c:15]2-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[F:22])[cH:23][n:24]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11]([CH:12]=[O:13])[cH:14][c:15]2-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[... | CB(O)O.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccc(Cl)nc2)c1 | Cc1ccc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2F)cn1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | e6427a06cf763f629ade010ec8edb6d572dcafeb9186c64e3948e154bc0e8e0d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[CH3;D1;+0:6]>>[CH3;D1;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 39 | [{"value": 39.0, "product": "FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.9, "product": "FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | DAY | Under an argon atmosphere, a mixture of 1-[(6-chloropyridin-3-yl)sulfonyl]-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (365 mg), methylboronic acid (90 mg), tetrakis(triphenylphosphine)palladium (116 mg), potassium carbonate (691 mg) and 1,4-dioxane (25 mL) was stirred at 80° C. for 3 days. The reaction mixture was po... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cc[nH]c1.c1ccccc1 | HCl.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | 80 | 72 | CB(O)O.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccc(Cl)nc2)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>Cc1ccc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2F)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eee68b78c04747ad87d7082d10851e72 | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1ccccn1>>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccccn2)c1 | FC1=C(C=CC=C1)C1=CC(=CN1)C=O.N1=C(C=CC=C1)S(=O)(=O)Cl>>FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C1=NC=CC=C1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[nH:13][cH:23]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][n:22]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][n:22]2)[cH:23]1 | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1ccccn1 | O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccccn2)c1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1ccccn1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[O;D1;H0:8]=[C:9]-[c:10]1:[c:11]:[nH;D2;+0:12]:[c:13](-[c:14]):[c:15]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[#7;a:6]:[c:7])-[n;H0;D3;+0:12]1:[c:11]:[c:10](-[C:9]=[O;D1;H0:8]):[c:15]:[c:13]:1-[c:14] | 55 | [{"value": 55.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar reaction as in Reference Example 65 and using 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (190 mg) and pyridine-2-sulfonyl chloride (231 mg), the title compound was obtained as a pale-red solid (yield 183 mg, 55%).
Conditions: See reaction.notes.procedure_details.
Workup: By a similar reaction as in Refer... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | null | null | null | O=Cc1c[nH]c(-c2ccccc2F)c1.O=S(=O)(Cl)c1ccccn1>>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2ccccn2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c914aeb94624ef5875a34038c36d1db | Cn1cc(S(=O)(=O)Cl)cn1.O=Cc1c[nH]c(-c2ccccc2F)c1>>Cn1cc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2F)cn1 | FC1=C(C=CC=C1)C1=CC(=CN1)C=O.CN1N=CC(=C1)S(=O)(=O)Cl>>FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NN(C1)C)C=O | Cl[S:5]([c:4]1[cH:3][n:2]([CH3:1])[n:23][cH:22]1)(=[O:6])=[O:7].[nH:8]1[cH:9][c:10]([CH:11]=[O:12])[cH:13][c:14]1-[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[F:21]>>[CH3:1][n:2]1[cH:3][c:4]([S:5](=[O:6])(=[O:7])[n:8]2[cH:9][c:10]([CH:11]=[O:12])[cH:13][c:14]2-[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[F:21])[cH:22][n:23... | Cn1cc(S(=O)(=O)Cl)cn1.O=Cc1c[nH]c(-c2ccccc2F)c1 | Cn1cc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2F)cn1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cn[nH]c1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]:1.[O;D1;H0:10]=[C:11]-[c:12]1:[c:13]:[c:14](-[c:15]):[nH;D2;+0:16]:[c:17]:1>>[C;D1;H3:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[n;H0;D3;+0:16]2:[c:17]:[c:12](-[C:11]=[O;D1;H0:10]):[c:13]... | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 65 and using 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (189 mg) and 1-methyl-1H-pyrazole-4-sulfonyl chloride (217 mg), the title compound was obtained as yellow crystals (yield 217 mg, 65%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cn[nH]c1.c1cc[nH]c1.c1ccccc1 | HCl | null | null | null | Cn1cc(S(=O)(=O)Cl)cn1.O=Cc1c[nH]c(-c2ccccc2F)c1>>Cn1cc(S(=O)(=O)n2cc(C=O)cc2-c2ccccc2F)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5d0744914ac468f95ac2ef397a43598 | Cc1ccccc1-c1cc(C=O)c[nH]1.O=S(=O)(Cl)c1cccnc1>>Cc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 | CC1=C(C=CC=C1)C1=CC(=CN1)C=O.[H-].[Na+].C1COCCOCCOCCOCCO1.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl>>CC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]([CH:11]=[O:12])[cH:13][nH:14]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]([CH:11]=[O:12])[cH:13][n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23... | Cc1ccccc1-c1cc(C=O)c[nH]1.O=S(=O)(Cl)c1cccnc1 | Cc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 | null | null | O1CCCC1.CN(C=O)C | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[n;H0;D3;+0:13](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]):[c:14](-[c:15]):[c:16]:1 | 80 | [{"value": 80.0, "product": "CC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.7, "product": "CC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 5-(2-methylphenyl)-1H-pyrrole-3-carbaldehyde (371 mg) in tetrahydrofuran (10 mL) were added sodium hydride (60% in oil, 288 mg) and 15-crown-5 (1.32 g) at room temperature. After stirring for 5 min, a suspension of pyridine-3-sulfonyl chloride hydrochloride (642 mg) in N,N-dimethylformamide (5 mL) was ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HCl | O1CCCC1.CN(C=O)C | null | 0.083333 | Cc1ccccc1-c1cc(C=O)c[nH]1.O=S(=O)(Cl)c1cccnc1>O1CCCC1.CN(C=O)C>Cc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-48d90f1e13ab4a4a9e015ba08e35838e | O=Cc1c[nH]c(-c2ccccc2F)c1Cl.O=S(=O)(Cl)c1cccnc1>>O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1Cl | [H-].[Na+].ClC=1C(=CNC1C1=C(C=CC=C1)F)C=O.C1COCCOCCOCCOCCO1.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl>>ClC=1C(=CN(C1C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1)C=O | [O:1]=[CH:2][c:3]1[cH:4][nH:5][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[F:22])[c:23]1[Cl:24].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][n:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[F:22])[c... | O=Cc1c[nH]c(-c2ccccc2F)c1Cl.O=S(=O)(Cl)c1cccnc1 | O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1Cl | null | null | O1CCCC1.O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[nH;D2;+0:15]:[c:16]:1>>[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[n;H0;D3;+0:15](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]):[c:16]:1 | 78.5 | [{"value": 78.0, "product": "ClC=1C(=CN(C1C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "ClC=1C(=CN(C1C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | A suspension of sodium hydride (60% in oil, 216 mg) in tetrahydrofuran (5 mL) was cooled to 0° C., a solution of 4-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (335 mg) in tetrahydrofuran (5 mL), 15-crown-5 (991 mg), and pyridine-3-sulfonyl chloride hydrochloride (482 mg) were added at 10° C. or below. After sti... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1.c1ccccc1 | HCl | O1CCCC1.O | 0 | 0.25 | O=Cc1c[nH]c(-c2ccccc2F)c1Cl.O=S(=O)(Cl)c1cccnc1>O1CCCC1.O>O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-59a530d5cab849db9d60677d4cd7b986 | O=C1CCC(=O)N1Cl.O=Cc1cc(-c2c(F)cccc2F)n(S(=O)(=O)c2cccnc2)c1>>O=Cc1cc(-c2c(F)cccc2F)n(S(=O)(=O)c2cccnc2)c1Cl | FC1=C(C(=CC=C1)F)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O.ClN1C(CCC1=O)=O.O>>ClC=1N(C(=CC1C=O)C1=C(C=CC=C1F)F)S(=O)(=O)C=1C=NC=CC1 | O=C1CCC(=O)N1[Cl:25].[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[c:7]([F:8])[cH:9][cH:10][cH:11][c:12]2[F:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:24]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[c:7]([F:8])[cH:9][cH:10][cH:11][c:12]2[F:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:... | O=C1CCC(=O)N1Cl.O=Cc1cc(-c2c(F)cccc2F)n(S(=O)(=O)c2cccnc2)c1 | O=Cc1cc(-c2c(F)cccc2F)n(S(=O)(=O)c2cccnc2)c1Cl | null | null | O1CCCC1.CN(C=O)C | Functional Group Interconversion | Chlorination | d90c51e04980e4fd5c41f2d9df1deefa5e01053fdb0009dabf82d5beacca27ac | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#16:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6](-[C:7]=[O;D1;H0:8]):[cH;D2;+0:9]:1>>[#16:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c;H0;D3;+0:9]:1-[Cl;H0;D1;+0:1] | 58.2 | [{"value": 58.0, "product": "ClC=1N(C(=CC1C=O)C1=C(C=CC=C1F)F)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.2, "product": "ClC=1N(C(=CC1C=O)C1=C(C=CC=C1F)F)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a solution of 5-(2,6-difluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (250 mg) in tetrahydrofuran (10 mL) and N,N-dimethylformamide (10 mL) was added N-chlorosuccinimide (1.06 g) and the mixture was stirred for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1.c1ccccc1.c1ccncc1 | HO- | O1CCCC1.CN(C=O)C | null | 15 | O=C1CCC(=O)N1Cl.O=Cc1cc(-c2c(F)cccc2F)n(S(=O)(=O)c2cccnc2)c1>O1CCCC1.CN(C=O)C>O=Cc1cc(-c2c(F)cccc2F)n(S(=O)(=O)c2cccnc2)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-134dee9a914249bf8e51a4af82d15f95 | O=C1CCC(=O)N1Cl.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1>>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1Cl | C(O)([O-])=O.[Na+].FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O.ClN1C(CCC1=O)=O>>ClC=1N(C(=CC1C=O)C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1 | O=C1CCC(=O)N1[Cl:24].[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[cH:23]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][n:2... | O=C1CCC(=O)N1Cl.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1 | O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1Cl | null | null | CN(C=O)C | Functional Group Interconversion | Chlorination | d90c51e04980e4fd5c41f2d9df1deefa5e01053fdb0009dabf82d5beacca27ac | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#16:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6](-[C:7]=[O;D1;H0:8]):[cH;D2;+0:9]:1>>[#16:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c;H0;D3;+0:9]:1-[Cl;H0;D1;+0:1] | 68.4 | [{"value": 68.0, "product": "ClC=1N(C(=CC1C=O)C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "ClC=1N(C(=CC1C=O)C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (331 mg) in N,N-dimethylformamide (33 mL) was added N-chlorosuccinimide (268 mg) and the mixture was stirred at 60° C. for 1 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1.c1ccccc1.c1ccncc1 | HO- | CN(C=O)C | 60 | 1 | O=C1CCC(=O)N1Cl.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1>CN(C=O)C>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1Cl |
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