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-c3a75813d0b24864aa4f7cd526efd6aa | ord-8953b4f38d7b445f9e098e54c522ab57 | Cc1ccc(Br)nc1>>Cc1ccc(C#N)nc1 | BrC1=NC=C(C=C1)C.CN(C)C=O>>CC=1C=CC(=NC1)C#N | Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:9][n:8]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]#[N:7])[n:8][cH:9]1 | Cc1ccc(Br)nc1 | Cc1ccc(C#N)nc1 | null | [C-]#N.[C-]#N.[Zn+2].[Zn] | null | Miscellaneous | OtherReaction | 8bb970223fb9058022a1c0cc1f9e538de973681a8f3a5dcbab2e4e1d78c06c44 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 57.6 | [{"value": 57.6, "product": "CC=1C=CC(=NC1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromo-5-methylpyridine ((8.6 g, 50 mmol) was mixed with Zn(CN)2 (4.1 g, 35 mmol), Pd(dppf)2C12 (0.89 g, mmol) and zinc dust (0.14 g, mmol) in DMF (86 ml) at 155° C. for 15 minutes. The reaction mixture was cooled down to room temperature and quenched with water and ethyl acetate. The mixture was filtered through celi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | [C-]#N.[C-]#N.[Zn+2].[Zn] | null | null | Cc1ccc(Br)nc1>[C-]#N.[C-]#N.[Zn+2].[Zn]>Cc1ccc(C#N)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d3afec238354a63b559e2c8eeda65b0 | CC(Cl)OC(=O)Cl.CCOC(=O)C1CC(C)=CCN1C(c1ccccc1)c1ccccc1>>CCOC(=O)C1CC(C)CCN1.Cl | ClCCl.C(C)OC(=O)C1N(CC=C(C1)C)C(C1=CC=CC=C1)C1=CC=CC=C1.ClC(=O)OC(C)Cl>>Cl.C(C)OC(=O)C1NCCC(C1)C | CC(Cl)OC(=O)[Cl:13].c1ccc(C(c2ccccc2)[N:12]2[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][C:8]([CH3:9])=[CH:10][CH2:11]2)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH:8]([CH3:9])[CH2:10][CH2:11][NH:12]1.[ClH:13] | CC(Cl)OC(=O)Cl.CCOC(=O)C1CC(C)=CCN1C(c1ccccc1)c1ccccc1 | CCOC(=O)C1CC(C)CCN1.Cl | null | [Pd] | CO | Miscellaneous | OtherReaction | 69216d61edd2f517e91aeedd10329993183da59fe828a9da52b9a9049b821fdd | 8680972761abf0bd12e62e23250487041204d99e9f76a29275e470fb95a71c86 | C1CCNCC1 | C-C(-Cl)-O-C(=O)-[Cl;H0;D1;+0:1].[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C;H0;D3;+0:8](-[C;D1;H3:9])=[CH;D2;+0:10]-[C:11]-[N;H0;D3;+0:12]-1-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[CH;D3;+0:8](-[C;D1;H3:9])-[CH2;D2;+0:10]-[C:11]-[NH;D2;+0:12]-1.[ClH;D0;+0:1] | null | [] | null | null | 8 | HOUR | To a dichloromethane (50 mL) solution of 1-benzhydryl-4-methyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid ethyl ester *(5.0 g, 14.9 mmol), 1-chloroethyl chloroformate (2.13 g, 14.9 mmol) was added at room temperature under argon. The reaction mixture was stirred overnight. After the reaction mixture was mixed with m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Ether.Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1=CC[NH]CC1 | C1CCNCC1 | C1CCNCC1 | HCl | [Pd].CO | null | 8 | CC(Cl)OC(=O)Cl.CCOC(=O)C1CC(C)=CCN1C(c1ccccc1)c1ccccc1>[Pd].CO>CCOC(=O)C1CC(C)CCN1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b04a569322c9446191de98fea4a5dc0b | CC(C)(C)OC(=O)C1NC(C(=O)O)CS1.N#Cc1cccc(C(=N)NO)c1>>CC(C)(C)OC(=O)N1CSC[C@@H]1c1nc(-c2cccc(C#N)c2)no1 | CC(C)(C)OC(=O)C1NC(CS1)C(=O)O.C(C(C)C)OC(=O)Cl.CN1CCOCC1.C(#N)C=1C=C(C(=N)NO)C=CC1.CN1CCOCC1.CN(C)C=O>>C(C)(C)(C)OC(=O)N1CSC[C@@H]1C1=NC(=NO1)C1=CC(=CC=C1)C#N | O=[C:13](O)[CH:12]1[NH:8][CH:9]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[S:10][CH2:11]1.[NH:14]=[C:15]([c:16]1[cH:17][cH:18][cH:19][c:20]([C:21]#[N:22])[cH:23]1)[NH:24][OH:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][S:10][CH2:11][C@@H:12]1[c:13]1[n:14][c:15](-[c:16]2[cH:17][cH:18][cH:19]... | CC(C)(C)OC(=O)C1NC(C(=O)O)CS1.N#Cc1cccc(C(=N)NO)c1 | CC(C)(C)OC(=O)N1CSC[C@@H]1c1nc(-c2cccc(C#N)c2)no1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 9a3f1cdb494e4e37488c15c0b335d0d12de31f3cf6e25f051ec62b6eab213bdb | 5f8fb8d44cab5012ae337e6f7839d766b6670181bed6e3027e9ff9ac28b68844 | c1ccc(-c2noc([C@H]3CSCN3)n2)cc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2]1-[C:3]-[#16:4]-[CH;D3;+0:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[NH;D2;+0:13]-1.[NH;D1;+0:14]=[C;H0;D3;+0:15](-[NH;D2;+0:16]-[OH;D1;+0:17])-[c;H0;D3;+0:18](:[c:19]:[c:20]):[c:21]:[c:22]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])... | 20 | [{"value": 20.0, "product": "C(C)(C)(C)OC(=O)N1CSC[C@@H]1C1=NC(=NO1)C1=CC(=CC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | 4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(S)-thiazolidine-3-carboxylic acid tert-butyl ester (212 mg, 20%, yellow oil) was prepared according to the procedure in Example 25 from Boc-L-thiazolidine-4-carboxylic acid (696 mg, 2.98 mmol) with isobutylchloroformate (0.43 ml, 3.28 mmol) and N-methylmorpholine (0.36 ml, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Secondary amine.Secondary amine.Monosulfide.Boc | Carbamic ester.Ether.Monosulfide.Boc | C1CSCN1 | C1CSC[NH]1.c1ncon1 | C1CSC[NH]1.c1ncon1.c1ccccc1 | HO- | C1CCOC1 | 120 | null | CC(C)(C)OC(=O)C1NC(C(=O)O)CS1.N#Cc1cccc(C(=N)NO)c1>C1CCOC1>CC(C)(C)OC(=O)N1CSC[C@@H]1c1nc(-c2cccc(C#N)c2)no1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-03587de826fc494386ac1305b85cf946 | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O.N#Cc1cccc(C(=N)NO)c1>>CC(C)(C)OC(=O)N1CCC[C@H]1c1nc(-c2cccc(C#N)c2)no1 | C(C)(C)(C)OC(=O)N1[C@@H](CCC1)C(=O)O.ClC(=O)OCC(C)C.C(#N)C=1C=C(C(=N)NO)C=CC1.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=CC(=CC=C1)C#N | O=[C:13](O)[C@H:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]1.[NH:14]=[C:15]([c:16]1[cH:17][cH:18][cH:19][c:20]([C:21]#[N:22])[cH:23]1)[NH:24][OH:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[c:13]1[n:14][c:15](-[c:16]2[cH:17][cH:18][cH... | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O.N#Cc1cccc(C(=N)NO)c1 | CC(C)(C)OC(=O)N1CCC[C@H]1c1nc(-c2cccc(C#N)c2)no1 | null | null | CN(C)C=O.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2noc([C@@H]3CCCN3)n2)cc1 | O-[C;H0;D3;+0:1](=O)-[C:2](-[C:3])-[#7:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12].[NH;D1;+0:13]=[C;H0;D3;+0:14](-[NH;D2;+0:15]-[OH;D1;+0:16])-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:20]:[c:21]>>[C:3]-[C:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c;H0;D3;+0:14](-[c;H0;D3;+0:17](:[c:18]:[... | 44 | [{"value": 44.0, "product": "C(C)(C)(C)OC(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=CC(=CC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.0, "product": "C(C)(C)(C)OC(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=CC(=CC=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | (S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (698 mg, 44%) was prepared according to the procedure in Example 25 from (S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (1.00 g, 4.66 mmol) with isobutyl chloroformate (0.64 mL, 4.9 mmol) and triethylamine (1.6 mL,... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | C1CC[NH]C1.c1ncon1.c1ccccc1 | HO- | CN(C)C=O.C1CCOC1 | 120 | null | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O.N#Cc1cccc(C(=N)NO)c1>CN(C)C=O.C1CCOC1>CC(C)(C)OC(=O)N1CCC[C@H]1c1nc(-c2cccc(C#N)c2)no1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-360a41b080bd4cfe8db20293b3a3bb42 | CC(C)(C)OC(=O)N1CCC[C@H]1c1nc(-c2cccc(C#N)c2)no1>>N#Cc1cccc(-c2noc([C@@H]3CCCN3)n2)c1 | C(C)(C)(C)OC(=O)N1[C@@H](CCC1)C1=NC(=NO1)C1=CC(=CC=C1)C#N>>N1[C@@H](CCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1 | CC(C)(C)OC(=O)[N:16]1[C@H:12]([c:11]2[o:10][n:9][c:8](-[c:7]3[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18]3)[n:17]2)[CH2:13][CH2:14][CH2:15]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][o:10][c:11]([C@@H:12]3[CH2:13][CH2:14][CH2:15][NH:16]3)[n:17]2)[cH:18]1 | CC(C)(C)OC(=O)N1CCC[C@H]1c1nc(-c2cccc(C#N)c2)no1 | N#Cc1cccc(-c2noc([C@@H]3CCCN3)n2)c1 | null | null | ClCCl.FC(C(=O)O)(F)F | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2noc([C@@H]3CCCN3)n2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[c:6](:[#7;a:7]):[#8;a:8]:[#7;a:9]>>[#7;a:7]:[c:6](-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1):[#8;a:8]:[#7;a:9] | 73.1 | [{"value": 73.0, "product": "N1[C@@H](CCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.1, "product": "N1[C@@H](CCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-3-(5-Pyrrolidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile (360 mg, 73%) was prepared according to the procedure in Example 39 from (S)-2-[3-(3-cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (697 mg, 2.05 mmol) in dichloromethane (15 mL) and trifluoroacetic acid (2.4 mL) at room t... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1ccccc1.c1ncon1.C1CCNC1 | HO- | ClCCl.FC(C(=O)O)(F)F | null | null | CC(C)(C)OC(=O)N1CCC[C@H]1c1nc(-c2cccc(C#N)c2)no1>ClCCl.FC(C(=O)O)(F)F>N#Cc1cccc(-c2noc([C@@H]3CCCN3)n2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fdbefcf0e0f64ddbb5e36be66ab81301 | CC(C)(C)OC(=O)N1CC=C[C@H]1c1nc(-c2cccc(C#N)c2)no1>>N#Cc1cccc(-c2noc([C@@H]3C=CCN3)n2)c1 | C(C)N(CC)CC.C(C)(C)(C)OC(=O)N1[C@@H](C=CC1)C1=NC(=NO1)C1=CC(=CC=C1)C#N.C(C)(C)(C)OC(=O)N1[C@@H](C=CC1)C(=O)O.C(#N)C=1C=C(C(=N)NO)C=CC1.ClC(=O)OCC(C)C>>N1[C@@H](C=CC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1 | CC(C)(C)OC(=O)[N:16]1[C@H:12]([c:11]2[o:10][n:9][c:8](-[c:7]3[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18]3)[n:17]2)[CH:13]=[CH:14][CH2:15]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][o:10][c:11]([C@@H:12]3[CH:13]=[CH:14][CH2:15][NH:16]3)[n:17]2)[cH:18]1 | CC(C)(C)OC(=O)N1CC=C[C@H]1c1nc(-c2cccc(C#N)c2)no1 | N#Cc1cccc(-c2noc([C@@H]3C=CCN3)n2)c1 | null | null | CN(C)C=O.C1CCOC1 | Reduction | Boc amine deprotection | 3db1a45a88a417910bbecbea3514681d70bf9e867667e9270e42a1947a8e0faf | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C1=C[C@@H](c2nc(-c3ccccc3)no2)NC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]=[C:4]-[C:5]-1-[c:6](:[#7;a:7]):[#8;a:8]:[#7;a:9]>>[#7;a:7]:[c:6](-[C:5]1-[C:4]=[C:3]-[C:2]-[NH;D2;+0:1]-1):[#8;a:8]:[#7;a:9] | null | [] | 120 | CELSIUS | null | null | (S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (372 mg, 42%, slightly impure) was prepared according to the procedure in Example 25 from (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester (557.8 mg, 2.62 mmol) with isobutyl chloroformate (0.36 mL, 2... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1=CC[NH]C1 | C1=CCNC1 | c1ccccc1.c1ncon1.C1=CCNC1 | HO- | CN(C)C=O.C1CCOC1 | 120 | null | CC(C)(C)OC(=O)N1CC=C[C@H]1c1nc(-c2cccc(C#N)c2)no1>CN(C)C=O.C1CCOC1>N#Cc1cccc(-c2noc([C@@H]3C=CCN3)n2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1c91f3cf7b3e433fb4bee9e1b9f6d676 | CC1CCN(C(=O)OC(C)(C)C)C(C(=O)O)C1.N=C(NO)c1cccc(Cl)c1>>C[C@@H]1CCN[C@@H](c2nc(-c3cccc(Cl)c3)no2)C1 | ClC(=O)OCC(C)C.ClC=1C=C(C(=N)NO)C=CC1.C(C)(C)(C)OC(=O)N1C(CC(CC1)C)C(=O)O.C(C)(C)(C)OC(=O)N1C(CC(CC1)C)C1=NC(=NO1)C1=CC(=CC=C1)Cl.FC(C(=O)O)(F)F.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N1C(CC(CC1)C)C1=NC(=NO1)C1=CC(=CC=C1)Cl.ClC=1C=C(C=CC1)C1=NOC(=N1)[C@@H]1NCC[C@H](C1)C | CC(C)(C)OC(=O)[N:31]1[CH2:30][CH2:29][CH:28]([CH3:27])[CH2:45][CH:32]1[C:33](=O)O.[NH:34]=[C:35]([c:36]1[cH:37][cH:38][cH:39][c:40]([Cl:41])[cH:42]1)[NH:43][OH:44]>>[CH3:27][C@@H:28]1[CH2:29][CH2:30][NH:31][C@@H:32]([c:33]2[n:34][c:35](-[c:36]3[cH:37][cH:38][cH:39][c:40]([Cl:41])[cH:42]3)[n:43][o:44]2)[CH2:45]1 | CC1CCN(C(=O)OC(C)(C)C)C(C(=O)O)C1.N=C(NO)c1cccc(Cl)c1 | C[C@@H]1CCN[C@@H](c2nc(-c3cccc(Cl)c3)no2)C1 | null | null | ClCCl.CN(C)C=O.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | b71b1bd831421a9fca4b2444b2a954eab5ab54ffface64916a57c987772fb8c5 | b1a52fb0c119c97183b7051188968cdae4178be967e11023a9e42edeae65635d | c1ccc(-c2noc([C@H]3CCCCN3)n2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-[CH;D3;+0:6]-1-[C;H0;D3;+0:7](-O)=O.[NH;D1;+0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[OH;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[c:14]:[c:13]:[c;H0;D3;+0:12](-[c;H0;D3;+0:9]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:7](-[C@H;D3;+0:6]2-[C:5]-[C:4]-[C:3]-[C:2]-[N... | 70 | [{"value": 33.9, "product": "C(C)(C)(C)OC(=O)N1C(CC(CC1)C)C1=NC(=NO1)C1=CC(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.0, "product": "ClC=1C=C(C=CC1)C1=NOC(=N1)[C@@H]1NCC[C@H](C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 30 | MINUTE | 2-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (320 mg, 33.9%) was prepared according to the procedure in Example 25 from 4-methyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (607.5 mg, 2.5 mmol), triethylamine (1.01 g, 10 mmol) with isobutyl chloroformate (... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1.c1ncon1 | C1CCNCC1.c1ncon1.c1ccccc1 | HO- | ClCCl.CN(C)C=O.C1CCOC1 | 130 | 0.5 | CC1CCN(C(=O)OC(C)(C)C)C(C(=O)O)C1.N=C(NO)c1cccc(Cl)c1>ClCCl.CN(C)C=O.C1CCOC1>C[C@@H]1CCN[C@@H](c2nc(-c3cccc(Cl)c3)no2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-372a76eb36294bcea2534834fde7aae0 | CC1CCCN(C(=O)OC(C)(C)C)C1C(=O)O.N=C(NO)c1cccc(Cl)c1>>CC1CCCNC1c1nc(-c2cccc(C#N)c2)no1 | C(C)(C)(C)OC(=O)N1C(C(CCC1)C)C(=O)O.C(C)N(CC)CC.ClC=1C=C(C(=N)NO)C=CC1.ClC(=O)OCC(C)C>>CC1C(NCCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1 | CC(C)(C)OC(=O)[N:6]1[CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH:7]1[C:8](=O)O.Cl[c:11]1[cH:12][cH:13][cH:14][c:15]([C:16](=[NH:17])[NH:19][OH:20])[cH:18]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6][CH:7]1[c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18]2)[n:19][o:20]1 | CC1CCCN(C(=O)OC(C)(C)C)C1C(=O)O.N=C(NO)c1cccc(Cl)c1 | CC1CCCNC1c1nc(-c2cccc(C#N)c2)no1 | null | null | CN(C)C=O.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 2f1bc33db8861423fabfa16a4e1371a6be2ebff8cf02720608c8b47f9b0b3ee1 | a53d96ab8610113ad78ca6ca1a1166f37e5de672e8f80a04de30adc6144f5fc4 | c1ccc(-c2noc(C3CCCCN3)n2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C;H0;D3;+0:5](-O)=O)-[C:6].Cl-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[c:11](-[C;H0;D3;+0:12](=[NH;D1;+0:13])-[NH;D2;+0:14]-[OH;D1;+0:15]):[c:16]:1>>[C:6]-[C:4](-[c;H0;D3;+0:5]1:[#7;a:17]:[c:18](-[c;H0;D3;+0:7]2:[c:8]:[c:9]:[c:10]:[c:11](-[C;H0;D2;+0:12]#[N;H0;D1;+0:1... | 77.8 | [{"value": 77.8, "product": "CC1C(NCCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.5, "product": "CC1C(NCCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 135 | CELSIUS | 30 | MINUTE | 2-[3-(3-cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (150 mg, 14.7%) was obtained as described in Example 25 from 3-methyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (672 mg, 2.765 mmol) with triethylamine (1.1 g, 11 mmol) in THF (8 mL) with isobutyl chloroformate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Carboxylic acid.Ether.Secondary amine.Boc | Nitrile.Secondary amine | C1CC[NH]CC1.c1ccccc1 | C1CCNCC1.c1ncon1.c1ccccc1 | C1CCNCC1.c1ncon1.c1ccccc1 | HCl | CN(C)C=O.C1CCOC1 | 135 | 0.5 | CC1CCCN(C(=O)OC(C)(C)C)C1C(=O)O.N=C(NO)c1cccc(Cl)c1>CN(C)C=O.C1CCOC1>CC1CCCNC1c1nc(-c2cccc(C#N)c2)no1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e854f20d87a8459eb201cbef7ecd8e22 | N#Cc1cccc(-c2noc([C@@H]3CCCN3)n2)c1.O=Cc1nccs1>>N#Cc1cccc(-c2noc([C@@H]3CCCN3Cc3nccs3)n2)c1 | N1[C@@H](CCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1.S1C(=NC=C1)C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>S1C(=NC=C1)CN1[C@@H](CCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][o:10][c:11]([C@@H:12]3[CH2:13][CH2:14][CH2:15][NH:16]3)[n:23]2)[cH:24]1.O=[CH:17][c:18]1[n:19][cH:20][cH:21][s:22]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][o:10][c:11]([C@@H:12]3[CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][c:18]3[n:19][cH:20][cH:21][s:22]3... | N#Cc1cccc(-c2noc([C@@H]3CCCN3)n2)c1.O=Cc1nccs1 | N#Cc1cccc(-c2noc([C@@H]3CCCN3Cc3nccs3)n2)c1 | null | null | ClC(C)Cl | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2noc([C@@H]3CCCN3Cc3nccs3)n2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1.[#7;a:7]:[c:8](-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1):[#8;a:14]:[#7;a:15]>>[#7;a:7]:[c:8](-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1):[#8;a:14]:[#7;a:15] | null | [] | null | null | null | null | 3-[5-(1-Thiazol-2-ylmethyl-pyrrolidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile (63.5 mg, 91%) was obtained as described in Example 43 from (S)-3-(5-pyrrolidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile (49.8 mg, 0.18 mmol) reacted with thiazole-2-carbaldehyde (35.2 mg, 0.31 mmol) and sodium triacetoxyborohydride (72 mg,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ncon1.C1CC[NH]C1.c1cscn1 | Other | ClC(C)Cl | null | null | N#Cc1cccc(-c2noc([C@@H]3CCCN3)n2)c1.O=Cc1nccs1>ClC(C)Cl>N#Cc1cccc(-c2noc([C@@H]3CCCN3Cc3nccs3)n2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5f6dc2a9f20a42b79cede1a3f8881294 | CC1CCCNC1c1nc(-c2cccc(C#N)c2)no1.O=Cc1ccccn1>>C[C@H]1CCCN(Cc2ccccn2)[C@H]1c1nc(-c2cccc(C#N)c2)no1 | CC1C(NCCC1)C1=NC(=NO1)C=1C=C(C#N)C=CC1.N1=C(C=CC=C1)C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C[C@@H]1[C@@H](N(CCC1)CC1=NC=CC=C1)C1=NC(=NO1)C=1C=C(C#N)C=CC1 | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6][CH:14]1[c:15]1[n:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][c:22]([C:23]#[N:24])[cH:25]2)[n:26][o:27]1.O=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1>>[CH3:1][C@H:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[C@H:14]1[c:15]1[n:16][c:17](-[c:18]2[... | CC1CCCNC1c1nc(-c2cccc(C#N)c2)no1.O=Cc1ccccn1 | C[C@H]1CCCN(Cc2ccccn2)[C@H]1c1nc(-c2cccc(C#N)c2)no1 | null | null | ClC(C)Cl | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2noc([C@H]3CCCCN3Cc3ccccn3)n2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-[CH;D3;+0:12]-1-[c:13]1:[#7;a:14]:[c:15]:[#7;a:16]:[#8;a:17]:1>>[C;D1;H3:6]-[C:7]1-[C:8]-[C:9]-[C:10]-[N;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5])-[C@H;D3;+0:12]-1-[c:13]1:[#7;a:14]:[c:15]:[#7;a:16]:[#8;a:17]... | 51.5 | [{"value": 51.5, "product": "C[C@@H]1[C@@H](N(CCC1)CC1=NC=CC=C1)C1=NC(=NO1)C=1C=C(C#N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.5, "product": "C[C@@H]1[C@@H](N(CCC1)CC1=NC=CC=C1)C1=NC(=NO1)C=1C=C(C#N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction was carried out as described in Example 43 from 3-[5-(3-methyl-piperidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile (29 mg, 0.108 mmol) with pyridine-2-carbaldehyde (13.9 mg, 0.13 mmol) and sodium triacetoxyborohydride (34.3 mg, 0.162 mmol) in dichloroethane (2 mL) to give cis-3-[5-(3-Methyl-1-pyridin-2-ylm... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccncc1.c1ncon1.c1ccccc1 | Other | ClC(C)Cl | null | null | CC1CCCNC1c1nc(-c2cccc(C#N)c2)no1.O=Cc1ccccn1>ClC(C)Cl>C[C@H]1CCCN(Cc2ccccn2)[C@H]1c1nc(-c2cccc(C#N)c2)no1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b5bd9a23d704fe3a036863bea719c8b | Clc1cccc(-c2noc(C3COCCN3)n2)c1.O=Cc1nccs1>>Clc1cccc(-c2noc(C3COCCN3Cc3nccs3)n2)c1 | ClC=1C=C(C=CC1)C1=NOC(=N1)C1NCCOC1.S1C(=NC=C1)C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>ClC=1C=C(C=CC1)C1=NOC(=N1)C1N(CCOC1)CC=1SC=CN1 | [Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][o:9][c:10]([CH:11]3[CH2:12][O:13][CH2:14][CH2:15][NH:16]3)[n:23]2)[cH:24]1.O=[CH:17][c:18]1[n:19][cH:20][cH:21][s:22]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][o:9][c:10]([CH:11]3[CH2:12][O:13][CH2:14][CH2:15][N:16]3[CH2:17][c:18]3[n:19][cH:20][cH:21][s:22]3)[n:... | Clc1cccc(-c2noc(C3COCCN3)n2)c1.O=Cc1nccs1 | Clc1cccc(-c2noc(C3COCCN3Cc3nccs3)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | 073d98e7dcd77aafeef71a76da7e61b2751c934600f6fff04db700a08f3e4453 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2noc(C3COCCN3Cc3nccs3)n2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1.[#7;a:7]:[c:8](-[C:9]1-[C:10]-[#8:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1):[#8;a:15]:[#7;a:16]>>[#7;a:7]:[c:8](-[C:9]1-[C:10]-[#8:11]-[C:12]-[C:13]-[N;H0;D3;+0:14]-1-[CH2;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1):[#8;a:15]:[#7;a:16] | null | [] | null | null | null | null | 3-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-4-pyridin-2-ylmethyl-morpholine was obtained as described in Example 43 from (48 mg, 44%) 3-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-morpholine (80 mg, 0.30 mmol) with 2-thiazolecarboxaldehyde (68 mg, 0.60) and sodium triacetoxyborohydride (89 mg, 0.42 mmol). The product... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.c1ncon1.C1COCC[NH]1.c1cscn1 | Other | null | null | null | Clc1cccc(-c2noc(C3COCCN3)n2)c1.O=Cc1nccs1>>Clc1cccc(-c2noc(C3COCCN3Cc3nccs3)n2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c7f2c59b0c024907b116881ff0d47bac | Cl>>Cl | CN(C1=NC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1.Cl>>Cl.CN(C1=NC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1 | [ClH:26]>>[ClH:26] | Cl | Cl | null | null | CC(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 50 | CELSIUS | null | null | A mixture of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (6.0 g) and propan-2-ol (120 ml) was stirred and heated to 50° C. under a nitrogen atmosphere. A solution of hydrogen chloride in propan-2-ol (5-6 N, 5.0 ml) was added and the stirred mixture warmed to 70° C., at which point a clear ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(C)O | 50 | null | Cl>CC(C)O>Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea9123fbb35a4123bac91acc28583f4b | Cl>>Cl | CN(C1=NC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1.Cl>>Cl.CN(C1=NC=CC=C1)CCOC1=CC=C(CC2C(NC(S2)=O)=O)C=C1 | [ClH:26]>>[ClH:26] | Cl | Cl | null | null | CC(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 70 | CELSIUS | null | null | A mixture of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (4.0 g) and propan-2-ol (100 ml) was stirred and heated to 70° C. Concentrated hydrochloric acid (1.1 ml) was added to the stirred reaction mixture which was observed to give a clear solution after approximately 3 minutes. The stirre... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CC(C)O | 70 | null | Cl>CC(C)O>Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-36064edae2b34b68bc893389bcce80b2 | NNC(=O)c1cccnc1Oc1ccccc1.O=C(Cl)c1cccc(C(F)(F)F)c1>>O=C(NNC(=O)c1cccnc1Oc1ccccc1)c1cccc(C(F)(F)F)c1 | O(C1=CC=CC=C1)C1=C(C(=O)NN)C=CC=N1.FC(C=1C=C(C(=O)Cl)C=CC1)(F)F>>O(C1=CC=CC=C1)C1=NC=CC=C1C(=O)NNC(C1=CC(=CC=C1)C(F)(F)F)=O | [NH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.Cl[C:2](=[O:1])[c:20]1[cH:21][cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29]1>>[O:1]=[C:2]([NH:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][... | NNC(=O)c1cccnc1Oc1ccccc1.O=C(Cl)c1cccc(C(F)(F)F)c1 | O=C(NNC(=O)c1cccnc1Oc1ccccc1)c1cccc(C(F)(F)F)c1 | null | null | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | O=C(NNC(=O)c1cccnc1Oc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]:[c:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[NH2;D1;+0:12]>>[#7;a:6]:[c:7]:[c:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Alternatively, as shown in scheme 2, reaction of 2-phenoxy-nicotinic acid hydrazide with 3-trifluoromethyl-benzoyl chloride in the presence of a base such as pyridine produced N′-(2-phenoxypyridine-3-carbonyl)-3-(trifluoromethyl)benzhydrazide as the product.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | NNC(=O)c1cccnc1Oc1ccccc1.O=C(Cl)c1cccc(C(F)(F)F)c1>N1=CC=CC=C1>O=C(NNC(=O)c1cccnc1Oc1ccccc1)c1cccc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d53ea3fecb95455a97b9d3a291de302d | NNC(=O)c1cccc(C(F)(F)F)c1.O=C(Cl)c1cccnc1Oc1ccccc1>>O=C(NNC(=O)c1cccnc1Oc1ccccc1)c1cccc(C(F)(F)F)c1 | FC(C=1C=C(C(=O)NN)C=CC1)(F)F.O(C1=CC=CC=C1)C1=NC=CC=C1C(=O)Cl>>O(C1=CC=CC=C1)C1=NC=CC=C1C(=O)NNC(C1=CC(=CC=C1)C(F)(F)F)=O | [O:1]=[C:2]([NH:3][NH2:4])[c:20]1[cH:21][cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29]1.Cl[C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[O:1]=[C:2]([NH:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[O:13][c:14]1[cH:15][cH:16][cH:17][cH:18][... | NNC(=O)c1cccc(C(F)(F)F)c1.O=C(Cl)c1cccnc1Oc1ccccc1 | O=C(NNC(=O)c1cccnc1Oc1ccccc1)c1cccc(C(F)(F)F)c1 | null | null | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | O=C(NNC(=O)c1cccnc1Oc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[#8:6]):[#7;a:7]:[c:8].[NH2;D1;+0:9]-[#7:10]-[C:11](=[O;D1;H0:12])-[c:13]>>[#8:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[#7:10]-[C:11](=[O;D1;H0:12])-[c:13]):[c:4] | 54 | [{"value": 54.0, "product": "O(C1=CC=CC=C1)C1=NC=CC=C1C(=O)NNC(C1=CC(=CC=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.3, "product": "O(C1=CC=CC=C1)C1=NC=CC=C1C(=O)NNC(C1=CC(=CC=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(trifluoromethyl)benzhydrazide (102.1 mg, 0.5 mmol), 2-phenoxypyridine-3-carbonyl chloride (117 mg, 0.5 mmol) in pyridine (5 mL) was refluxed for 2 h. It was evaporated in vacuo and the residue was purified by column chromatography (silica gel, EtOAc/CH2Cl2=4:1) to give 107 mg (54%) of the title compoun... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | NNC(=O)c1cccc(C(F)(F)F)c1.O=C(Cl)c1cccnc1Oc1ccccc1>N1=CC=CC=C1>O=C(NNC(=O)c1cccnc1Oc1ccccc1)c1cccc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-008bb786951449e2b7c8e1014983b396 | NNC(=O)c1cccnc1Oc1ccccc1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Oc1ccccc1 | O(C1=CC=CC=C1)C1=NC=CC=C1C(=O)NN.FC(C=1C=C(C=O)C=CC1)(F)F.O>>FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)OC2=CC=CC=C2)C=CC1)(F)F | [O:1]=[C:2]([NH:3][NH2:4])[c:16]1[cH:17][cH:18][cH:19][n:20][c:21]1[O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1)[c:16]1[cH:17][cH:18][cH:1... | NNC(=O)c1cccnc1Oc1ccccc1.O=Cc1cccc(C(F)(F)F)c1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Oc1ccccc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1cccnc1Oc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[#7:10]-[NH2;D1;+0:11]>>[#7;a:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[#7:10]-[N;H0;D2;+0:11]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 92 | [{"value": 92.0, "product": "FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)OC2=CC=CC=C2)C=CC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)OC2=CC=CC=C2)C=CC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-phenoxypyridine-3-carboxylic acid hydrazide (913 mg, 4 mmol), 3-trifluoromethylbenzaldehyde (696 mg, 4 mmol) in ethanol (40 mL) was refluxed for 13 h. It was cooled to room temperature and some precipitate was observed. The mixture was diluted by water (40 mL) and the solid was collected by filtration a... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | C(C)O | null | null | NNC(=O)c1cccnc1Oc1ccccc1.O=Cc1cccc(C(F)(F)F)c1>C(C)O>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Oc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a444204e56cc495693ba2a36bb753350 | NN=Cc1cccc(C(F)(F)F)c1.O=C(Cl)c1cccnc1Cl>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Cl | ClC1=C(C(=O)Cl)C=CC=N1.FC(C=1C=C(C=NN)C=CC1)(F)F.CCN(CC)CC>>FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)Cl)C=CC1)(F)F | [NH2:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1.Cl[C:2](=[O:1])[c:16]1[cH:17][cH:18][cH:19][n:20][c:21]1[Cl:22]>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1)[c:16]1[cH:17][cH:18][cH:19][n:20][c:21]1[Cl:22] | NN=Cc1cccc(C(F)(F)F)c1.O=C(Cl)c1cccnc1Cl | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Cl | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e1e032c84f30f6c93cf688039f3cc62747a034583f6175d60f7a0e21b27b6064 | 863011cce7fa0c660ac34aaac93028d203ff6ffc4b5a2233660e564db26255d2 | O=C(NN=Cc1ccccc1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[NH2;D1;+0:9]-[#7:10]=[C:11]-[c:12]>>[Cl;D1;H0:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[#7:10]=[C:11]-[c:12]):[c:4] | 110.8 | [{"value": 90.0, "product": "FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)Cl)C=CC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 110.8, "product": "FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)Cl)C=CC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 2-chloro-nicotinoyl chloride (1.75 g, 10 mmol) in 40 mL THF was added 3-trifluoromethyl-benzylidene-hydrazine (1.88 g, 10 mmol) in 20 mL THF at 0° C., followed by 1.5 mL Et3N. The solution was stirred at room temperature overnight and precipitate was observed. It was filtered and the solid was ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazone | Hydrazone amide | null | null | c1ccccc1.c1ccncc1 | HCl | C1CCOC1 | null | 8 | NN=Cc1cccc(C(F)(F)F)c1.O=C(Cl)c1cccnc1Cl>C1CCOC1>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f8a56db2f8f49cd96e2a9135e82de0a | NNC(=O)c1cccnc1Nc1ccccc1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Nc1ccccc1 | N(C1=CC=CC=C1)C1=C(C(=O)NN)C=CC=N1.FC(C=1C=C(C=O)C=CC1)(F)F.O>>FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)NC2=CC=CC=C2)C=CC1)(F)F | [O:1]=[C:2]([NH:3][NH2:4])[c:16]1[cH:17][cH:18][cH:19][n:20][c:21]1[NH:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1)[c:16]1[cH:17][cH:18][cH:... | NNC(=O)c1cccnc1Nc1ccccc1.O=Cc1cccc(C(F)(F)F)c1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Nc1ccccc1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1cccnc1Nc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[#7:10]-[NH2;D1;+0:11]>>[#7;a:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[#7:10]-[N;H0;D2;+0:11]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 85 | [{"value": 85.0, "product": "FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)NC2=CC=CC=C2)C=CC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.0, "product": "FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)NC2=CC=CC=C2)C=CC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 2-anilino-nicotinic acid hydrazide (0.31 g, 1.05 mmol) in 20 mL EtOH was added 3-trifluoromethyl-benzaldehyde (0.182 g, 1.05 mmol) in 5 mL EtOH at room temperature. The mixture was refluxed for 4 h and cooled to room temperature, then diluted by 100 mL water. The precipitate was collected by fi... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | CCO | null | null | NNC(=O)c1cccnc1Nc1ccccc1.O=Cc1cccc(C(F)(F)F)c1>CCO>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Nc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-608d0829507d4b34996be2affd1c7dc2 | O=C(Cl)C(=O)Cl.O=C(O)c1cccnc1Oc1cccnc1>>O=C(Cl)c1cccnc1Oc1cccnc1 | N1=CC(=CC=C1)OC1=C(C(=O)O)C=CC=N1.C(C(=O)Cl)(=O)Cl>>N1=CC(=CC=C1)OC1=C(C(=O)Cl)C=CC=N1 | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[O:10][c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[O:10][c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1 | O=C(Cl)C(=O)Cl.O=C(O)c1cccnc1Oc1cccnc1 | O=C(Cl)c1cccnc1Oc1cccnc1 | null | null | C1CCOC1 | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc(Oc2cccnc2)nc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6](-[#8:7]):[#7;a:8]:[c:9]>>[#8:7]-[c:6](:[#7;a:8]:[c:9]):[c:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3]):[c:5] | null | [] | null | null | 3 | HOUR | To a stirred solution of 2-(pyridin-3-yloxy)-nicotinic acid (0.432 g, 2.0 mmol) in THF (15 mL) at 0° C. was added oxalylchloride (2 mL, 2M in CH2Cl2, 4.0 mmol) dropwise. The solution was stirred at room temperature for 3 h. The solvent was evaporated in vacuo to yield 2-(pyridin-3-yloxy)-nicotinoyl chloride as a solid.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccncc1.c1ccncc1 | HCl | C1CCOC1 | null | 3 | O=C(Cl)C(=O)Cl.O=C(O)c1cccnc1Oc1cccnc1>C1CCOC1>O=C(Cl)c1cccnc1Oc1cccnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b85e4707b7e14bc5916c2f41fb6f0b20 | NN=Cc1cccc(C(F)(F)F)c1.O=C(Cl)c1cccnc1Oc1cccnc1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Oc1cccnc1 | N1=CC(=CC=C1)OC1=C(C(=O)Cl)C=CC=N1.FC(C=1C=C(C=NN)C=CC1)(F)F>>FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)OC=2C=NC=CC2)C=CC1)(F)F | [NH2:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1.Cl[C:2](=[O:1])[c:16]1[cH:17][cH:18][cH:19][n:20][c:21]1[O:22][c:23]1[cH:24][cH:25][cH:26][n:27][cH:28]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1)[c:16]1[cH:17][cH:18][cH:19... | NN=Cc1cccc(C(F)(F)F)c1.O=C(Cl)c1cccnc1Oc1cccnc1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Oc1cccnc1 | null | null | CCN(CC)CC.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e1e032c84f30f6c93cf688039f3cc62747a034583f6175d60f7a0e21b27b6064 | 863011cce7fa0c660ac34aaac93028d203ff6ffc4b5a2233660e564db26255d2 | O=C(NN=Cc1ccccc1)c1cccnc1Oc1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[#8:6]):[#7;a:7]:[c:8].[NH2;D1;+0:9]-[#7:10]=[C:11]-[c:12]>>[#8:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[#7:10]=[C:11]-[c:12]):[c:4] | 55 | [{"value": 55.0, "product": "FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)OC=2C=NC=CC2)C=CC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 2-(pyridin-3-yloxy)-nicotinic acid (0.432 g, 2.0 mmol) in THF (15 mL) at 0° C. was added oxalylchloride (2 mL, 2M in CH2Cl2, 4.0 mmol) dropwise. The solution was stirred at room temperature for 3 h. The solvent was evaporated in vacuo to yield 2-(pyridin-3-yloxy)-nicotinoyl chloride as a solid.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazone | Hydrazone amide | null | null | c1ccccc1.c1ccncc1.c1ccncc1 | HCl | CCN(CC)CC.C1CCOC1 | null | null | NN=Cc1cccc(C(F)(F)F)c1.O=C(Cl)c1cccnc1Oc1cccnc1>CCN(CC)CC.C1CCOC1>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Oc1cccnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47adc2ac387f4000a9d9c47a18468d30 | NNC(=O)c1ccccc1-c1ccccc1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccccc1-c1ccccc1 | C=1(C(=CC=CC1)C(=O)NN)C1=CC=CC=C1.FC(C=1C=C(C=O)C=CC1)(F)F.O>>FC(C=1C=C(C=NNC(=O)C=2C(=CC=CC2)C2=CC=CC=C2)C=CC1)(F)F | [O:1]=[C:2]([NH:3][NH2:4])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1-[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1)[c:16]1[cH:17][cH:18][cH:19][c... | NNC(=O)c1ccccc1-c1ccccc1.O=Cc1cccc(C(F)(F)F)c1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccccc1-c1ccccc1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1ccccc1-c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[O;D1;H0:8]=[C:7](-[c:9])-[#7:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "FC(C=1C=C(C=NNC(=O)C=2C(=CC=CC2)C2=CC=CC=C2)C=CC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "FC(C=1C=C(C=NNC(=O)C=2C(=CC=CC2)C2=CC=CC=C2)C=CC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of biphenyl-2-carboxylic acid-hydrazide (0.212 g, 1.0 mmol) in 20 mL EtOH was added 3-trifluoromethyl-benzaldehyde (0.174 g, 1.0 mmol) in 5 mL EtOH at room temperature. The mixture was refluxed for 4 h and cooled to room temperature, then was diluted by 100 mL of water. The precipitate was collect... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CCO | null | null | NNC(=O)c1ccccc1-c1ccccc1.O=Cc1cccc(C(F)(F)F)c1>CCO>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccccc1-c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4dd49d2fe0d44c2586b5228a6ac889c0 | NNC(=O)c1cccnc1Nc1cccc(C(F)(F)F)c1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Nc1cccc(C(F)(F)F)c1 | FC(C=1C=C(C=CC1)NC1=C(C(=O)NN)C=CC=N1)(F)F.FC(C=1C=C(C=O)C=CC1)(F)F>>FC(C=1C=C(C=NNC(=O)C=2C(=NC=CC2)NC2=CC(=CC=C2)C(F)(F)F)C=CC1)(F)F | [O:1]=[C:2]([NH:3][NH2:4])[c:16]1[cH:17][cH:18][cH:19][n:20][c:21]1[NH:22][c:23]1[cH:24][cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:1... | NNC(=O)c1cccnc1Nc1cccc(C(F)(F)F)c1.O=Cc1cccc(C(F)(F)F)c1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Nc1cccc(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1cccnc1Nc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[#7:10]-[NH2;D1;+0:11]>>[#7;a:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[#7:10]-[N;H0;D2;+0:11]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared from 2-(3-trifluoromethyl-phenylamino)-nicotinic acid-hydrazide and 3-trifluoromethyl-benzaldehyde by a procedure similar to Example 22. 1H NMR (DMSO-d6): 12.30 (s, 1H), 10.58 (s, 1H), 8.53 (s, 1H), 8.45 (d, J=4.5 Hz, 1H), 8.31 (s, 1H), 8.24 (d, J=8.1 Hz, 1H), 8.12 (s, 1H), 8.06 (d, J=8.... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | null | null | null | NNC(=O)c1cccnc1Nc1cccc(C(F)(F)F)c1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cccnc1Nc1cccc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-740d8bd6beda43838111b48d42322c48 | COc1cc(C(=O)NN)cc(OC)c1OC.O=Cc1cccc(C(F)(F)F)c1>>COc1cc(C(=O)NN=Cc2cccc(C(F)(F)F)c2)cc(OC)c1OC | COC=1C=C(C(=O)NN)C=C(C1OC)OC.FC(C=1C=C(C=O)C=CC1)(F)F>>FC(C=1C=C(C=NNC(C2=CC(=C(C(=C2)OC)OC)OC)=O)C=CC1)(F)F | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][NH2:9])[cH:21][c:22]([O:23][CH3:24])[c:25]1[O:26][CH3:27].O=[CH:10][c:11]1[cH:12][cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][N:9]=[CH:10][c:11]2[cH:12][cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH... | COc1cc(C(=O)NN)cc(OC)c1OC.O=Cc1cccc(C(F)(F)F)c1 | COc1cc(C(=O)NN=Cc2cccc(C(F)(F)F)c2)cc(OC)c1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[O;D1;H0:8]=[C:7](-[c:9])-[#7:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared from 3,4,5-trimethoxy-benzoic acid hydrazide and 3-trifluoromethyl-benzaldehyde by a procedure similar to Example 22. 1H NMR (DMSO-d6): 11.93 (s, 1H), 8.57 (s, 1H), 8.08 (s, 1H), 8.05 (d, J=8.1 Hz, 1H), 7.82 (d, J=7.5 Hz, 1H), 7.74 (d, J=7.5 Hz, 1H), 7.26 (s, 2H), 3.89 (s, 6H), 3.75 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1cc(C(=O)NN)cc(OC)c1OC.O=Cc1cccc(C(F)(F)F)c1>>COc1cc(C(=O)NN=Cc2cccc(C(F)(F)F)c2)cc(OC)c1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f64e1ae01864728a883f24745eac144 | NNC(=O)c1ccc(O)c(O)c1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccc(O)c(O)c1 | OC=1C=C(C(=O)NN)C=CC1O.FC(C=1C=C(C=O)C=CC1)(F)F>>FC(C=1C=C(C=NNC(C2=CC(=C(C=C2)O)O)=O)C=CC1)(F)F | [O:1]=[C:2]([NH:3][NH2:4])[c:16]1[cH:17][cH:18][c:19]([OH:20])[c:21]([OH:22])[cH:23]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1)[c:16]1[cH:17][cH:18][c:19]([OH:20])[c:21]([OH:22])[cH:23... | NNC(=O)c1ccc(O)c(O)c1.O=Cc1cccc(C(F)(F)F)c1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccc(O)c(O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[O;D1;H0:8]=[C:7](-[c:9])-[#7:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared from 3,4-dihydroxy-benzoic acid hydrazide and 3-trifluoromethyl-benzaldehyde by a procedure similar to Example 22. 1H NMR (DMSO-d6): 11.79 (s, 1H), 9.55 (s, 1H), 9.28 (s, 1H), 8.50 (s, 1H), 8.04 (s, 1H), 8.0 (d, J=7.8 Hz, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.38 (d, J=2.... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | NNC(=O)c1ccc(O)c(O)c1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccc(O)c(O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5a134eddc954ecfae14562cfbab265a | NNC(=O)c1cnc(-c2ccccn2)nc1-c1ccncc1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cnc(-c2ccccn2)nc1-c1ccncc1 | N1=CC=C(C=C1)C1=NC(=NC=C1C(=O)NN)C1=NC=CC=C1.FC(C=1C=C(C=O)C=CC1)(F)F>>FC(C=1C=C(C=NNC(=O)C=2C(=NC(=NC2)C2=NC=CC=C2)C2=CC=NC=C2)C=CC1)(F)F | [O:1]=[C:2]([NH:3][NH2:4])[c:16]1[cH:17][n:18][c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][n:25]2)[n:26][c:27]1-[c:28]1[cH:29][cH:30][n:31][cH:32][cH:33]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14... | NNC(=O)c1cnc(-c2ccccn2)nc1-c1ccncc1.O=Cc1cccc(C(F)(F)F)c1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cnc(-c2ccccn2)nc1-c1ccncc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1cnc(-c2ccccn2)nc1-c1ccncc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]:[c:7](-[C:8](=[O;D1;H0:9])-[#7:10]-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:5]:[c:6]:[c:7](-[C:8](=[O;D1;H0:9])-[#7:10]-[N;H0;D2;+0:11]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | The title compound was prepared from 4-(pyridin-4-yl)-2-(pyridin-2-yl)pyrimidine-5-carboxylic acid-hydrazide and 3-trifluoromethyl-benzaldehyde by a procedure similar to Example 22. 1H NMR (DMSO-d6): 12.38 (s, 1H), 9.30 (s, 1H), 9.22 (s, 1H), 8.84 (m, 1H), 8.78 (d, J=6.0 Hz, 1H), 8.68 (d, J=6.0 Hz, 1H), 8.54 (m, 1H), 8... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1cncnc1.c1ccncc1.c1ccncc1 | HO- | null | null | null | NNC(=O)c1cnc(-c2ccccn2)nc1-c1ccncc1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cnc(-c2ccccn2)nc1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f49a17a3eb6649e293faacd09e4d45e6 | COC(=O)c1cc([N+](=O)[O-])ccc1Cl.Oc1ccccc1>>COC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 | C1(=CC=CC=C1)O.CC(C)([O-])C.[K+].COC(C1=C(C=CC(=C1)[N+](=O)[O-])Cl)=O>>COC(C1=C(C=CC(=C1)[N+](=O)[O-])OC1=CC=CC=C1)=O | Cl[c:13]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1.[OH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | COC(=O)c1cc([N+](=O)[O-])ccc1Cl.Oc1ccccc1 | COC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2]:[c:3] | 86 | [{"value": 86.0, "product": "COC(C1=C(C=CC(=C1)[N+](=O)[O-])OC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.9, "product": "COC(C1=C(C=CC(=C1)[N+](=O)[O-])OC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A mixture of phenol (5.64 g, 60 mmol) and potassium t-butoxide (6.74 g, 60 mmol) in 50 mL 1,4-dioxane was stirred at room temperature for 0.5 h. To the mixture was added 2-chloro-5-nitro-benzoic acid methyl ester (10.78 g, 50 mmol) and the mixture was refluxed overnight. The solvent was evaporated and the residue was p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | O1CCOCC1 | null | 0.5 | COC(=O)c1cc([N+](=O)[O-])ccc1Cl.Oc1ccccc1>O1CCOCC1>COC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1738e466431348c99be50780a38d6944 | COC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1>>COC(=O)c1cc(N)ccc1Oc1ccccc1 | COC(C1=C(C=CC(=C1)[N+](=O)[O-])OC1=CC=CC=C1)=O>>COC(C1=C(C=CC(=C1)N)OC1=CC=CC=C1)=O | O=[N+:8]([O-])[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:10][cH:9]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | COC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 | COC(=O)c1cc(N)ccc1Oc1ccccc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 94 | [{"value": 94.0, "product": "COC(C1=C(C=CC(=C1)N)OC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.9, "product": "COC(C1=C(C=CC(=C1)N)OC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of phenol (5.64 g, 60 mmol) and potassium t-butoxide (6.74 g, 60 mmol) in 50 mL 1,4-dioxane was stirred at room temperature for 0.5 h. To the mixture was added 2-chloro-5-nitro-benzoic acid methyl ester (10.78 g, 50 mmol) and the mixture was refluxed overnight. The solvent was evaporated and the residue was p... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].C(C)O | null | null | COC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1>[Pd].C(C)O>COC(=O)c1cc(N)ccc1Oc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-088a5e30a30747c2bf97dcbb7cfdb319 | COC(=O)c1cc(N)ccc1Oc1ccccc1.NN>>NNC(=O)c1cc(N)ccc1Oc1ccccc1 | COC(C1=C(C=CC(=C1)N)OC1=CC=CC=C1)=O.NN>>NC=1C=CC(=C(C(=O)NN)C1)OC1=CC=CC=C1 | CO[C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[O:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | COC(=O)c1cc(N)ccc1Oc1ccccc1.NN | NNC(=O)c1cc(N)ccc1Oc1ccccc1 | null | null | null | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccc(Oc2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[N;D1;H2:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 76 | [{"value": 76.0, "product": "NC=1C=CC(=C(C(=O)NN)C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of phenol (5.64 g, 60 mmol) and potassium t-butoxide (6.74 g, 60 mmol) in 50 mL 1,4-dioxane was stirred at room temperature for 0.5 h. To the mixture was added 2-chloro-5-nitro-benzoic acid methyl ester (10.78 g, 50 mmol) and the mixture was refluxed overnight. The solvent was evaporated and the residue was p... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)c1cc(N)ccc1Oc1ccccc1.NN>>NNC(=O)c1cc(N)ccc1Oc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9ce7d92de8c040388f83485ffb45c598 | NNC(=O)c1cc(N)ccc1Oc1ccccc1.O=Cc1cccc(C(F)(F)F)c1>>Nc1ccc(Oc2ccccc2)c(C(=O)NN=Cc2cccc(C(F)(F)F)c2)c1 | NC=1C=CC(=C(C(=O)NN)C1)OC1=CC=CC=C1.FC(C=1C=C(C=O)C=CC1)(F)F>>FC(C=1C=C(C=NNC(C2=C(C=CC(=C2)N)OC2=CC=CC=C2)=O)C=CC1)(F)F | [NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([C:14](=[O:15])[NH:16][NH2:17])[cH:29]1.O=[CH:18][c:19]1[cH:20][cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]([C:14](=[O:15])[NH:16][N:17]=... | NNC(=O)c1cc(N)ccc1Oc1ccccc1.O=Cc1cccc(C(F)(F)F)c1 | Nc1ccc(Oc2ccccc2)c(C(=O)NN=Cc2cccc(C(F)(F)F)c2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1ccccc1Oc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[O;D1;H0:8]=[C:7](-[c:9])-[#7:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of phenol (5.64 g, 60 mmol) and potassium t-butoxide (6.74 g, 60 mmol) in 50 mL 1,4-dioxane was stirred at room temperature for 0.5 h. To the mixture was added 2-chloro-5-nitro-benzoic acid methyl ester (10.78 g, 50 mmol) and the mixture was refluxed overnight. The solvent was evaporated and the residue was p... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | NNC(=O)c1cc(N)ccc1Oc1ccccc1.O=Cc1cccc(C(F)(F)F)c1>>Nc1ccc(Oc2ccccc2)c(C(=O)NN=Cc2cccc(C(F)(F)F)c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dfdc69b060d1471bae250b76da3f846d | BrCBr.COC(=O)c1ccccc1C>>COC(=O)c1ccccc1CBr | BrN1C(CCC1=O)=O.BrCBr.COC(C1=C(C=CC=C1)C)=O>>COC(C1=C(C=CC=C1)CBr)=O | BrC[Br:12].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH3:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][Br:12] | BrCBr.COC(=O)c1ccccc1C | COC(=O)c1ccccc1CBr | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | e416946138a933de2b30160c7a311cc11081d714c7fd688d8c7bfc4d7a43c64d | d9577ddf1932cd046d32b07c743cb92ab682a32530154b5760ce230c9695c76b | c1ccccc1 | Br-C-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH2;D2;+0:7]-[Br;H0;D1;+0:1]):[c:8] | 76.3 | [{"value": 76.0, "product": "COC(C1=C(C=CC=C1)CBr)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.3, "product": "COC(C1=C(C=CC=C1)CBr)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-bromosuccinimide, dibromomethane (3.56 g, 20 mmol) and methyl-2-methylbenzoate (3.04 g, 20 mmol) in 30 mL CHCl3 was refluxed for 4 h. The solvent was evaporated and the residue was purified by column chromatography, with EtOAc:hexanes, 1:5, as eluant, yielding (3.496 g, 76%) of 2-bromomethyl-benzoic aci... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | Primary halide | null | null | c1ccccc1 | HBr | C(Cl)(Cl)Cl | null | null | BrCBr.COC(=O)c1ccccc1C>C(Cl)(Cl)Cl>COC(=O)c1ccccc1CBr |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61772f1d9878452a9dab16a8c43c752c | C1COCCN1.COC(=O)c1ccccc1CBr>>COC(=O)c1ccccc1CN1CCOCC1 | COC(C1=C(C=CC=C1)CBr)=O.N1CCOCC1.Cl>>COC(C1=C(C=CC=C1)CN1CCOCC1)=O | [NH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1.Br[CH2:11][c:10]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][cH:9]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1 | C1COCCN1.COC(=O)c1ccccc1CBr | COC(=O)c1ccccc1CN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCOCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1):[c:3] | 38.3 | [{"value": 38.0, "product": "COC(C1=C(C=CC=C1)CN1CCOCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.3, "product": "COC(C1=C(C=CC=C1)CN1CCOCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-bromosuccinimide, dibromomethane (3.56 g, 20 mmol) and methyl-2-methylbenzoate (3.04 g, 20 mmol) in 30 mL CHCl3 was refluxed for 4 h. The solvent was evaporated and the residue was purified by column chromatography, with EtOAc:hexanes, 1:5, as eluant, yielding (3.496 g, 76%) of 2-bromomethyl-benzoic aci... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | CN(C)C=O | null | null | C1COCCN1.COC(=O)c1ccccc1CBr>CN(C)C=O>COC(=O)c1ccccc1CN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-318b3ad43e9a428a81846712b4d588f3 | COC(=O)c1ccccc1CN1CCOCC1.NN.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccccc1CN1CCOCC1 | COC(C1=C(C=CC=C1)CN1CCOCC1)=O.NN.FC(C=1C=C(C=O)C=CC1)(F)F>>FC(C=1C=C(C=NNC(C2=C(C=CC=C2)CN2CCOCC2)=O)C=CC1)(F)F | CO[C:2](=[O:1])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[CH2:22][N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1.[NH2:3][NH2:4].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1)[c:16]1[cH:17][c... | COC(=O)c1ccccc1CN1CCOCC1.NN.O=Cc1cccc(C(F)(F)F)c1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccccc1CN1CCOCC1 | null | null | null | Acylation | OtherReaction | 23aa60a9cb39edac54d30b37081a8ba315da7cde2ac0c401380bd99319581369 | dfe54355b76c234eb1c1f2927d18431a84369f0f82bb3db1d3c35cffa8e81d0b | O=C(NN=Cc1ccccc1)c1ccccc1CN1CCOCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9].[NH2;D1;+0:10]-[NH2;D1;+0:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:10]-[N;H0;D2;+0:11]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of N-bromosuccinimide, dibromomethane (3.56 g, 20 mmol) and methyl-2-methylbenzoate (3.04 g, 20 mmol) in 30 mL CHCl3 was refluxed for 4 h. The solvent was evaporated and the residue was purified by column chromatography, with EtOAc:hexanes, 1:5, as eluant, yielding (3.496 g, 76%) of 2-bromomethyl-benzoic aci... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde.Ester | Hydrazone amide | null | null | c1ccccc1.c1ccccc1.C1COCC[NH]1 | HO- | null | null | null | COC(=O)c1ccccc1CN1CCOCC1.NN.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccccc1CN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d7d36961e6324e4f8df1cfa79cab61f5 | COC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1.NN>>NNC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 | COC(C1=C(C=CC(=C1)[N+](=O)[O-])OC1=CC=CC=C1)=O.NN>>[N+](=O)([O-])C=1C=CC(=C(C(=O)NN)C1)OC1=CC=CC=C1 | CO[C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | COC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1.NN | NNC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 | null | null | null | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccc(Oc2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[N;D1;H2:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 74 | [{"value": 74.0, "product": "[N+](=O)([O-])C=1C=CC(=C(C(=O)NN)C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-nitro-2-phenoxy-benzoic acid methyl ester (4.0 g, 14.7 mmol) and hydrazine (5 mL, 80%) was refluxed for 4 h to yield 5-nitro-2-phenoxy-benzoic acid hydrazide (2.97 g, 74%). The title compound was prepared from 5-nitro-2-phenoxy-benzoic acid hydrazide and 3-trifluoromethyl-benzaldehyde by a procedure simi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1.NN>>NNC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c64b1bf0b934a24895eec8674a24d96 | NNC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 | [N+](=O)([O-])C=1C=CC(=C(C(=O)NN)C1)OC1=CC=CC=C1.FC(C=1C=C(C=O)C=CC1)(F)F>>FC(C=1C=C(C=NNC(C2=C(C=CC(=C2)[N+](=O)[O-])OC2=CC=CC=C2)=O)C=CC1)(F)F | [O:1]=[C:2]([NH:3][NH2:4])[c:16]1[cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22][cH:23][c:24]1[O:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1)[... | NNC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1.O=Cc1cccc(C(F)(F)F)c1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1ccccc1Oc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[O;D1;H0:8]=[C:7](-[c:9])-[#7:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 5-nitro-2-phenoxy-benzoic acid methyl ester (4.0 g, 14.7 mmol) and hydrazine (5 mL, 80%) was refluxed for 4 h to yield 5-nitro-2-phenoxy-benzoic acid hydrazide (2.97 g, 74%). The title compound was prepared from 5-nitro-2-phenoxy-benzoic acid hydrazide and 3-trifluoromethyl-benzaldehyde by a procedure simi... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | NNC(=O)c1cc([N+](=O)[O-])ccc1Oc1ccccc1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1cc([N+](=O)[O-])ccc1Oc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5bde9529dd004f679474b11da944cd48 | NNC(=O)c1ccccc1OCc1ncn(-c2cccc(Cl)n2)n1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccccc1OCc1ncn(-c2cccc(Cl)n2)n1 | ClC1=CC=CC(=N1)N1N=C(N=C1)COC1=C(C(=O)NN)C=CC=C1.FC(C=1C=C(C=O)C=CC1)(F)F>>FC(C=1C=C(C=NNC(C2=C(C=CC=C2)OCC2=NN(C=N2)C2=NC(=CC=C2)Cl)=O)C=CC1)(F)F | [O:1]=[C:2]([NH:3][NH2:4])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[O:22][CH2:23][c:24]1[n:25][cH:26][n:27](-[c:28]2[cH:29][cH:30][cH:31][c:32]([Cl:33])[n:34]2)[n:35]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12... | NNC(=O)c1ccccc1OCc1ncn(-c2cccc(Cl)n2)n1.O=Cc1cccc(C(F)(F)F)c1 | O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccccc1OCc1ncn(-c2cccc(Cl)n2)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccc1)c1ccccc1OCc1ncn(-c2ccccn2)n1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[O;D1;H0:8]=[C:7](-[c:9])-[#7:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared from 2-[1-(6-chloro-pyridin-2-yl)-1H-[1,2,4]triazol-3-ylmethoxy]-benzoic acid hydrazide and 3-trifluoromethyl-benzaldehyde by a procedure similar to Example 22. 1H NMR (DMSO-d6): 11.92 (s, 1H), 8.43 (s, 1H), 8.0 (m, 3H), 7.80 (m, 3H), 7.70 (t, J=7.5 Hz, 1H), 7.60 (m, J=7.5 Hz, 1H), 7.45 ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccccc1.c1ccccc1.c1nnc[nH]1.c1ccncc1 | HO- | null | null | null | NNC(=O)c1ccccc1OCc1ncn(-c2cccc(Cl)n2)n1.O=Cc1cccc(C(F)(F)F)c1>>O=C(NN=Cc1cccc(C(F)(F)F)c1)c1ccccc1OCc1ncn(-c2cccc(Cl)n2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b0c8094aa6dc4e63a19a2e4759db5c4b | CC(C)(C)C(=O)OCCl.Cc1cc(-c2nc(-c3ccc(OCC(C)C)c([N+](=O)[O-])c3)n[nH]2)ccn1>>Cc1cc(-c2nc(-c3ccc(OCC(C)C)c([N+](=O)[O-])c3)nn2COC(=O)C(C)(C)C)ccn1 | C(C)(=O)OCC.C(C(C)(C)C)(=O)OCCl.C([O-])([O-])=O.[K+].[K+].C(C(C)C)OC1=C(C=C(C=C1)C1=NNC(=N1)C1=CC(=NC=C1)C)[N+](=O)[O-]>>C(C(C)C)OC1=C(C=C(C=C1)C1=NN(C(=N1)C1=CC(=NC=C1)C)COC(C(C)(C)C)=O)[N+](=O)[O-] | Cl[CH2:24][O:25][C:26](=[O:27])[C:28]([CH3:29])([CH3:30])[CH3:31].[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH:14]([CH3:15])[CH3:16])[c:17]([N+:18](=[O:19])[O-:20])[cH:21]3)[n:22][nH:23]2)[cH:32][cH:33][n:34]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][c:... | CC(C)(C)C(=O)OCCl.Cc1cc(-c2nc(-c3ccc(OCC(C)C)c([N+](=O)[O-])c3)n[nH]2)ccn1 | Cc1cc(-c2nc(-c3ccc(OCC(C)C)c([N+](=O)[O-])c3)nn2COC(=O)C(C)(C)C)ccn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 341818133a655e086e52b94a1b4cf3b9f5b36b392ed6784d0bf2e5180bd7125c | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | c1ccc(-c2n[nH]c(-c3ccncc3)n2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[c:6]-[c:7]1:[#7;a:8]:[c:9](-[c:10]):[#7;a:11]:[nH;D2;+0:12]:1>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[#7;a:11]:[c:9](-[c:10]):[#7;a:8]:[c:7]:1-[c:6] | 76.4 | [{"value": 76.4, "product": "C(C(C)C)OC1=C(C=C(C=C1)C1=NN(C(=N1)C1=CC(=NC=C1)C)COC(C(C)(C)C)=O)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 354 mg of the powder obtained in Example 1 was dissolved in 3 ml of DMF, 181 mg of pivaloyloxymethyl chloride and 276 mg of potassium carbonate were added thereto, and the mixture was stirred at room temperature for 18 hours. Ethyl acetate was added to the reaction mixture, which was then washed with water and dried ov... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1nnc[nH]1 | c1nnc[nH]1 | c1ccncc1.c1nnc[nH]1.c1ccccc1 | HCl | CN(C)C=O | null | 18 | CC(C)(C)C(=O)OCCl.Cc1cc(-c2nc(-c3ccc(OCC(C)C)c([N+](=O)[O-])c3)n[nH]2)ccn1>CN(C)C=O>Cc1cc(-c2nc(-c3ccc(OCC(C)C)c([N+](=O)[O-])c3)nn2COC(=O)C(C)(C)C)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e7f36c0f126469e86546f58399ac2d6 | CCOC(=O)c1cc2cc(OC)c(OC)cc2[nH]1.Cc1ccccc1S>>CCOC(=O)c1[nH]c2cc(OC)c(OC)cc2c1Sc1ccccc1C | ClN1C(CCC1=O)=O.CC1=C(C=CC=C1)S.C(C)OC(=O)C=1NC2=CC(=C(C=C2C1)OC)OC>>C(C)OC(=O)C=1NC2=CC(=C(C=C2C1SC1=C(C=CC=C1)C)OC)OC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([O:14][CH3:15])[cH:16][c:17]2[cH:18]1.[SH:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([O:14][CH3:15])[cH:16][c:17]2[c:18]1[S:19][c:20]1[cH:... | CCOC(=O)c1cc2cc(OC)c(OC)cc2[nH]1.Cc1ccccc1S | CCOC(=O)c1[nH]c2cc(OC)c(OC)cc2c1Sc1ccccc1C | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 6d0ae58eb1269904d7dda169c1c9a22d9d8065e25d20aca85acf2d11bcd1657c | a20e50d7df818b91ffc2e826d304ad74f6246978a284c599e867e2d806b7437e | c1ccc(Sc2c[nH]c3ccccc23)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[cH;D2;+0:11]:1.[SH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11]:1-[S;H0;D2;+0:12]-[c:13](:[c:14]):[c:15] | 66 | [{"value": 66.0, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1SC1=C(C=CC=C1)C)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "C(C)OC(=O)C=1NC2=CC(=C(C=C2C1SC1=C(C=CC=C1)C)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a −78° C. solution of dichloromethane (30mL) and N-chlorosuccinimide was added 2-methyl benzenethiol (0.709 mL, 6.01 mmol) dropwise. The reaction was allowed to warm 0° C. and then stirred for 30 minutes. 5,6-dimethoxy-1H-indole-2-carboxylic acid ethyl ester (Lancaster Synthesis Inc., Windham, N.H.) (1.5 g, 6.01 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Monosulfide | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | ClCCl | 0 | 0.5 | CCOC(=O)c1cc2cc(OC)c(OC)cc2[nH]1.Cc1ccccc1S>ClCCl>CCOC(=O)c1[nH]c2cc(OC)c(OC)cc2c1Sc1ccccc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb5d94843e66410cb44db9aeca8b6b7b | CCOC(=O)c1[nH]c2cc(OC)c(OC)cc2c1Sc1ccccc1.CI.Sc1ccccc1>>CCOC(=O)c1[nH]c2cc(OC)c(OC)cc2c1Sc1ccccc1.CCOC(=O)c1c(Sc2ccccc2)c2cc(OC)c(OC)cc2n1C | IC.C1(=CC=CC=C1)S.C(C)OC(=O)C=1NC2=CC(=C(C=C2C1SC1=CC=CC=C1)OC)OC.[H-].[Na+]>>C(C)OC(=O)C=1NC2=CC(=C(C=C2C1SC1=CC=CC=C1)OC)OC.C(C)OC(=O)C=1N(C2=CC(=C(C=C2C1SC1=CC=CC=C1)OC)OC)C | [O:3]=[C:4]([c:6]1[nH:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([O:14][CH3:15])[cH:16][c:17]2[c:18]1[S:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[O:28][CH2:27][CH3:26].I[CH3:51].[cH:1]1[cH:35][c:34]([SH:33])[cH:39][cH:38][cH:37]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13... | CCOC(=O)c1[nH]c2cc(OC)c(OC)cc2c1Sc1ccccc1.CI.Sc1ccccc1 | CCOC(=O)c1[nH]c2cc(OC)c(OC)cc2c1Sc1ccccc1.CCOC(=O)c1c(Sc2ccccc2)c2cc(OC)c(OC)cc2n1C | null | null | O1CCCC1.CN(C=O)C.C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 9713abebfb8e51a1032fb9121050eca2010af6f9fd447564542de77f5085f56f | f822852f717c3f99eef3c9005dcae0244fe62f7adcf966447a025720182d77e7 | c1ccc(Sc2c[nH]c3ccccc23)cc1.c1ccc(Sc2c[nH]c3ccccc23)cc1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[C:3]-[O;H0;D2;+0:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[c:7](:[c:8]):[#7;a:9]:[c:10].[SH;D1;+0:11]-[c:12]1:[c:13]:[c:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[C;D1;H3:2]-[C:3]-[O;H0;D2;+0:4]-[C:18](=[O;D1;H0:19])-[c:20]1:[#7;a:21](-[CH3;D1;+0:1]):[c:22]:[c:23]:[c:24]:1-[S;H0;D2;+0:11]-... | null | [] | null | null | null | null | To a 0° C. tetrahydrofuran solution of 5,6-dimethoxy-3-phenylsulfanyl-1H-indole-2-carboxylic acid ethyl ester (0.500 g, 1.40 mmol) was added sodium hydride (95%, 0.037 g, 1.54 mmol) followed by iodomethane (0.096 mL, 1.54 mmol). 5,6-dimethoxy-3-phenylsulfanyl-1H-indole-2-carboxylic acid ethyl ester was synthesized in a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic thiol | Ester.Ester.Ether.Ether.Monosulfide | c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | I- | O1CCCC1.CN(C=O)C.C(C)(=O)OCC | null | null | CCOC(=O)c1[nH]c2cc(OC)c(OC)cc2c1Sc1ccccc1.CI.Sc1ccccc1>O1CCCC1.CN(C=O)C.C(C)(=O)OCC>CCOC(=O)c1[nH]c2cc(OC)c(OC)cc2c1Sc1ccccc1.CCOC(=O)c1c(Sc2ccccc2)c2cc(OC)c(OC)cc2n1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1af1d6e48acc44038280d9abc9a403e4 | Brc1ccc2cc[nH]c2c1.OB(O)c1ccc(OC(F)(F)F)cc1>>FC(F)(F)Oc1ccc(-c2ccc3cc[nH]c3c2)cc1 | BrC1=CC=C2C=CNC2=C1.FC(OC1=CC=C(C=C1)B(O)O)(F)F.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C>>FC(OC1=CC=C(C=C1)C1=CC=C2C=CNC2=C1)(F)F | Br[c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][nH:16][c:17]2[cH:18]1.OB(O)[c:9]1[cH:8][cH:7][c:6]([O:5][C:2]([F:1])([F:3])[F:4])[cH:20][cH:19]1>>[F:1][C:2]([F:3])([F:4])[O:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][nH:16][c:17]3[cH:18]2)[cH:19][cH:20]1 | Brc1ccc2cc[nH]c2c1.OB(O)c1ccc(OC(F)(F)F)cc1 | FC(F)(F)Oc1ccc(-c2ccc3cc[nH]c3c2)cc1 | 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.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:[c:7]):[c:8]:1.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[c:7]:[#7;a:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:8]:1 | 51 | [{"value": 51.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of 6-bromo-1H-indole (1.22 g, 6.22 mmol), 4-trifluoromethoxyphenyl boronic acid (1.41 g, 6.84 mmol), tetrakis(triphenylphosphine)palladium (0.213 g, 0.184 mmol) and sodium carbonate (2.64 g, 24.9 mmoles) in water (12.5 mL), ethanol (4 mL), and toluene (25 mL) was heated at reflux for 1.5 hours then cooled t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | 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.C(C)O | null | null | Brc1ccc2cc[nH]c2c1.OB(O)c1ccc(OC(F)(F)F)cc1>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.C(C)O>FC(F)(F)Oc1ccc(-c2ccc3cc[nH]c3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a8a7341dc2a4e8ea4bfec29e65a0923 | CI.FC(F)(F)Oc1ccc(-c2ccc3cc[nH]c3c2)cc1>>Cn1ccc2ccc(-c3ccc(OC(F)(F)F)cc3)cc21 | Cl.IC.FC(OC1=CC=C(C=C1)C1=CC=C2C=CNC2=C1)(F)F.[H-].[Na+]>>FC(OC1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C)(F)F | I[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([O:13][C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]3)[cH:20][c:21]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([O:13][C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]3)[cH:20][c:21]12 | CI.FC(F)(F)Oc1ccc(-c2ccc3cc[nH]c3c2)cc1 | Cn1ccc2ccc(-c3ccc(OC(F)(F)F)cc3)cc21 | null | null | O.C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2707f3725991b3e30363eaf960bacae3914d2ac8cb498ed736c8bd8efed63caa | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | I-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | null | [] | null | null | 30 | MINUTE | To a solution of 6-(4-trifluoromethoxyphenyl)-1H-indole (0.853, 3.08 mmoles) in dry THF (10 mL) was added sodium hydride (60% dispersion on mineral oil, 0.47 g, 12.3 mmol), portionwise. The reaction mixture was stirred under nitrogen for 30 minutes and, then cooled in ice bath. A solution of iodomethane (0.38 mL, 6.1 m... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | HI | O.C1CCOC1 | null | 0.5 | CI.FC(F)(F)Oc1ccc(-c2ccc3cc[nH]c3c2)cc1>O.C1CCOC1>Cn1ccc2ccc(-c3ccc(OC(F)(F)F)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9471eaa61f3143c9abc8259361719ea8 | CO.Cn1ccc2ccc(-c3ccc(OC(F)(F)F)cc3)cc21.O=C(Cl)C(=O)Cl>>COC(=O)C(=O)c1cn(C)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12 | CO.FC(OC1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C)(F)F.C(C(=O)Cl)(=O)Cl.C([O-])(O)=O.[Na+]>>FC(OC1=CC=C(C=C1)C1=CC=C2C(=CN(C2=C1)C)C(C(=O)OC)=O)(F)F | [CH3:1][OH:2].[cH:7]1[cH:8][n:9]([CH3:10])[c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]3)[cH:25][cH:26][c:27]12.Cl[C:3](=[O:4])[C:5](Cl)=[O:6]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[c:7]1[cH:8][n:9]([CH3:10])[c:11]2[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([O:18][... | CO.Cn1ccc2ccc(-c3ccc(OC(F)(F)F)cc3)cc21.O=C(Cl)C(=O)Cl | COC(=O)C(=O)c1cn(C)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 264e15ef638d5923d9cdb37238e03379dedc35f81790e2b78e2e58dbb2677ac4 | f98da691c0dfb324c2f1bcb126ca61672eaf52552bbb5f2a49d51be135db8558 | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[OH;D1;+0:14]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:14]-[C;D1;H3:13]):[c:9](:[c:10]):[c:11]:1:... | 50 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 6-(4-trifluoromethoxyphenyl)-1-methyl-1H-indole (0.304 g, 1.04 mmol) in dry THF (5 mL) under nitrogen at 0° C. was added oxalyl chloride (0.11 ml, 1.2 mmol). The reaction mixture was stirred at room temperature for 2 hour. The mixture was cooled in an ice bath. Methanol (1 mL) was added. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Methanol | Ketone.Ester | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | HCl | C1CCOC1 | null | 2 | CO.Cn1ccc2ccc(-c3ccc(OC(F)(F)F)cc3)cc21.O=C(Cl)C(=O)Cl>C1CCOC1>COC(=O)C(=O)c1cn(C)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6cbfadf8a16d47548e663a040fca9cd7 | COC(=O)C(=O)c1cn(C)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12>>Cn1cc(C(=O)C(=O)O)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc21 | Cl.FC(OC1=CC=C(C=C1)C1=CC=C2C(=CN(C2=C1)C)C(C(=O)OC)=O)(F)F.[OH-].[Na+].O>>CN1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O | C[O:9][C:7]([C:5]([c:4]1[cH:3][n:2]([CH3:1])[c:26]2[c:10]1[cH:11][cH:12][c:13](-[c:14]1[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]1)[cH:25]2)=[O:6])=[O:8]>>[CH3:1][n:2]1[cH:3][c:4]([C:5](=[O:6])[C:7](=[O:8])[OH:9])[c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([O:18][C:19]([F:20])([... | COC(=O)C(=O)c1cn(C)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12 | Cn1cc(C(=O)C(=O)O)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc21 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 59.4 | [{"value": 59.1, "product": "CN1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "CN1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | The mixture of methyl 2-[6-(4-trifluoromethoxyphenyl)-1 -methyl-1H-indol-3-yl]-2-oxoacetate (0.120 g, 0.318 mmol), and sodium hydroxide (1N, 1 mL, 1.0 mmol) in methanol (10 mL), was stirred at room temperature for 2.5 hours. The mixture was poured into excess water and acidified with 1N hydrochloric acid. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2cc[nH]c2c1.c1ccccc1 | Other | CO | null | 2.5 | COC(=O)C(=O)c1cn(C)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12>CO>Cn1cc(C(=O)C(=O)O)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0383f094cf274dcb95ace383024d4ee3 | Brc1ccc2cc[nH]c2c1.CI>>Cn1ccc2ccc(Br)cc21 | Cl.[H-].[Na+].BrC1=CC=C2C=CNC2=C1.IC>>BrC1=CC=C2C=CN(C2=C1)C | [nH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]12.I[CH3:1]>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]12 | Brc1ccc2cc[nH]c2c1.CI | Cn1ccc2ccc(Br)cc21 | null | null | O.C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2707f3725991b3e30363eaf960bacae3914d2ac8cb498ed736c8bd8efed63caa | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc2[nH]ccc2c1 | I-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | 81.6 | [{"value": 81.6, "product": "BrC1=CC=C2C=CN(C2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.6, "product": "BrC1=CC=C2C=CN(C2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 6-bromo-1H-indole (2.34 g, 11.9 mmol) in dry THF (25 mL) was cooled in an ice bath. Sodium hydride (1.12 g of 60% dispersion in oil, 28.0 mmol) was added. The mixture was stirred for 30 minutes under nitrogen at room temperature, then cooled in an ice bath. Iodomethane (1.6 mL, 26 mmol) was added. The rea... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | HI | O.C1CCOC1 | null | 0.5 | Brc1ccc2cc[nH]c2c1.CI>O.C1CCOC1>Cn1ccc2ccc(Br)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7aa04fa7a1d941f58696ec2df52813c5 | Cn1ccc2ccc(Br)cc21.OB(O)c1ccc(C(F)(F)F)cc1>>Cn1ccc2ccc(-c3ccc(C(F)(F)F)cc3)cc21 | BrC1=CC=C2C=CN(C2=C1)C.FC(C1=CC=C(C=C1)B(O)O)(F)F.C([O-])([O-])=O.[Na+].[Na+]>>FC(C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C)(F)F | Br[c:8]1[cH:7][cH:6][c:5]2[cH:4][cH:3][n:2]([CH3:1])[c:20]2[cH:19]1.OB(O)[c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]1>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]3)[cH:19][c:20]12 | Cn1ccc2ccc(Br)cc21.OB(O)c1ccc(C(F)(F)F)cc1 | Cn1ccc2ccc(-c3ccc(C(F)(F)F)cc3)cc21 | 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.C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | e5ead5b904b0190a128418d7442173388e9e1f8d91c97a5f7a23f024c91c663c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:6]:[c:5]:[c:4]:1 | 51 | [{"value": 51.0, "product": "FC(C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.8, "product": "FC(C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of 6-bromo-1-methyl-1H-indole (0.216 g, 1.03 mmol), 4-trifluoromethylbenzeneboronic acid (0.216 g, 1.14 mmol), tetrakis(triphenylphosphine)palladium (0.0541 g, 0.0468 mmol) and sodium carbonate (0.438 g, 4.13 mmol) in water (2.5 mL), ethanol (1 mL) and toluene (5 mL) was refluxed for 1.6 hours. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.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.O.C1(=CC=CC=C1)C.C(C)O | null | null | Cn1ccc2ccc(Br)cc21.OB(O)c1ccc(C(F)(F)F)cc1>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.C1(=CC=CC=C1)C.C(C)O>Cn1ccc2ccc(-c3ccc(C(F)(F)F)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7479e990707d4b4784c2e721d1c59ad6 | Brc1ccc2cc[nH]c2c1.CCI>>CCn1ccc2ccc(Br)cc21 | Cl.[H-].[Na+].BrC1=CC=C2C=CNC2=C1.ICC>>BrC1=CC=C2C=CN(C2=C1)CC | [nH:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]12.I[CH2:2][CH3:1]>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]12 | Brc1ccc2cc[nH]c2c1.CCI | CCn1ccc2ccc(Br)cc21 | null | null | O.C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 082ff5e2bbe1b14d00a5f44aa77c96a44849f09b23e40a195ca75be81235dc53 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ccc2c1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[c:3]:[c:4]1:[c:5]:[c:6]:[c:7]:[nH;D2;+0:8]:1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[c:6]:[c:5]:[c:4]:1:[c:3] | 71 | [{"value": 71.0, "product": "BrC1=CC=C2C=CN(C2=C1)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.4, "product": "BrC1=CC=C2C=CN(C2=C1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 35 | MINUTE | A solution of 6-bromoindole (1.01 g, 5.15 mmol) in THF (10 mL) was cooled in an ice bath. Sodium hydride (0.459 g of 60% dispersion in oil, 11.5 mmol) was added. After stirring for 35 minutes at room temperature under nitrogen, the reaction mixture was again cooled in an ice bath, and iodoethane (0.90 mL, 11 mmol) was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | HI | O.C1CCOC1 | null | 0.583333 | Brc1ccc2cc[nH]c2c1.CCI>O.C1CCOC1>CCn1ccc2ccc(Br)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-45e5b1a9ddf64a26a95f49533153fcca | CCn1ccc2ccc(Br)cc21.OB(O)c1ccc(OC(F)(F)F)cc1>>CCn1ccc2ccc(-c3ccc(OC(F)(F)F)cc3)cc21 | BrC1=CC=C2C=CN(C2=C1)CC.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C.FC(OC1=CC=C(C=C1)B(O)O)(F)F>>FC(OC1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)CC)(F)F | Br[c:9]1[cH:8][cH:7][c:6]2[cH:5][cH:4][n:3]([CH2:2][CH3:1])[c:22]2[cH:21]1.OB(O)[c:10]1[cH:11][cH:12][c:13]([O:14][C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([O:14][C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[cH:21][c:22]12 | CCn1ccc2ccc(Br)cc21.OB(O)c1ccc(OC(F)(F)F)cc1 | CCn1ccc2ccc(-c3ccc(OC(F)(F)F)cc3)cc21 | 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.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | e5ead5b904b0190a128418d7442173388e9e1f8d91c97a5f7a23f024c91c663c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1):[#7;a:7](-[C:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[#7;a:7](:[c:9]):[c:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:6]:[c:5]:[c:4]:1 | 56 | [{"value": 56.0, "product": "FC(OC1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)CC)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.8, "product": "FC(OC1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)CC)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Step 2 of Example 2, 6-bromo-1-ethyl-1H-indole (0.410 g , 1.83 mmol) was reacted with 4-trifluoromethoxybenzene boronic acid (0.422 g, 2.05 mmol), using tetrakis(triphenylphosphine)palladium (0.0651 g, 0.0563 mmol), and sodium carbonate (0.792 g, 7.47 mmol) in water (3.7 mL), ethano... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.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.O.C(C)O | null | null | CCn1ccc2ccc(Br)cc21.OB(O)c1ccc(OC(F)(F)F)cc1>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.C(C)O>CCn1ccc2ccc(-c3ccc(OC(F)(F)F)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-81109514eb0f4102b13602cee0779bfb | CCn1ccc2ccc(Br)cc21.OB(O)c1ccc(C(F)(F)F)cc1>>CCn1ccc2ccc(-c3ccc(C(F)(F)F)cc3)cc21 | BrC1=CC=C2C=CN(C2=C1)CC.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C.FC(C1=CC=C(C=C1)B(O)O)(F)F>>FC(C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)CC)(F)F | Br[c:9]1[cH:8][cH:7][c:6]2[cH:5][cH:4][n:3]([CH2:2][CH3:1])[c:21]2[cH:20]1.OB(O)[c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]3)[cH:20][c:21]12 | CCn1ccc2ccc(Br)cc21.OB(O)c1ccc(C(F)(F)F)cc1 | CCn1ccc2ccc(-c3ccc(C(F)(F)F)cc3)cc21 | 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.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | e5ead5b904b0190a128418d7442173388e9e1f8d91c97a5f7a23f024c91c663c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1):[#7;a:7](-[C:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[#7;a:7](:[c:9]):[c:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:6]:[c:5]:[c:4]:1 | 56.1 | [{"value": 56.0, "product": "FC(C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)CC)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.1, "product": "FC(C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)CC)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Step 2 of Example 2, 6-bromo-1-ethyl-1H-indole (0.400 g , 1.78 mmol), was coupled to 4-trifluoromethylbenzene boronic acid (0.348 g, 1.83 mmol), using tetrakis(triphenylphosphine)palladium (0.0668 g, 0.0578 mmol), and sodium carbonate (0.769 g, 7.26 mmol) in water (3.6 mL), ethanol ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.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.O.C(C)O | null | null | CCn1ccc2ccc(Br)cc21.OB(O)c1ccc(C(F)(F)F)cc1>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.C(C)O>CCn1ccc2ccc(-c3ccc(C(F)(F)F)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7509f087bdc9406885e12a17f0944485 | CCn1cc(C(=O)C(=O)[O-])c2ccc(-c3ccc(C(F)(F)F)cc3)cc21>>CCn1cc(C(=O)C(=O)O)c2ccc(-c3ccc(C(F)(F)F)cc3)cc21 | FC(C1=CC=C(C=C1)C1=CC=C2C(=CN(C2=C1)CC)C(C(=O)OCC)=O)(F)F.[OH-].[Na+].FC(C1=CC=C(C=C1)C1=CC=C2C(=CN(C2=C1)CC)C(C(=O)[O-])=O)(F)F>>C(C)N1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)C(F)(F)F)C(C(=O)O)=O | [CH3:1][CH2:2][n:3]1[cH:4][c:5]([C:6](=[O:7])[C:8](=[O:9])[O-:10])[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]3)[cH:25][c:26]12>>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([C:6](=[O:7])[C:8](=[O:9])[OH:10])[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19]([F:20... | CCn1cc(C(=O)C(=O)[O-])c2ccc(-c3ccc(C(F)(F)F)cc3)cc21 | CCn1cc(C(=O)C(=O)O)c2ccc(-c3ccc(C(F)(F)F)cc3)cc21 | null | null | CO | Reduction | Carboxylate to carboxylic acid | 65edb34f59b888c9ecb87d6c8e9fd76d082de6afc49403d96c457f834c73148e | 222e2311064b3cb906d6bdeba44711f5dada050c096bbbcc7b35038975f228e8 | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C:6](=[O;D1;H0:8])-[OH;D1;+0:7] | null | [] | null | null | null | null | Following the procedure described in Step 4 of Example 2, using ethyl 2-[6-(4-trifluoromethylphenyl)-1-ethyl-1H-indol-3-yl]-2-oxoacetate (0.0987 g, 0.253 mmol), and 1N sodium hydroxide (0.76 mL, 0.76 mmol) in methanol (5 mL), 2-[6-(4-trifluoromethylphenyl)-1-ethyl-1H-indol-3-yl]-2-oxoacetate acid (0.0714 g, 78%) was pr... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccc2cc[nH]c2c1.c1ccccc1 | null | CO | null | null | CCn1cc(C(=O)C(=O)[O-])c2ccc(-c3ccc(C(F)(F)F)cc3)cc21>CO>CCn1cc(C(=O)C(=O)O)c2ccc(-c3ccc(C(F)(F)F)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-20705c9a2cab4139889f816b65b7013a | BrCc1ccccc1.Brc1ccc2cc[nH]c2c1>>Brc1ccc2ccn(Cc3ccccc3)c2c1 | Cl.[H-].[Na+].BrC1=CC=C2C=CNC2=C1.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)Br | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[Br:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][nH:8][c:16]2[cH:17]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][n:8]([CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]2[cH:17]1 | BrCc1ccccc1.Brc1ccc2cc[nH]c2c1 | Brc1ccc2ccn(Cc3ccccc3)c2c1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 082ff5e2bbe1b14d00a5f44aa77c96a44849f09b23e40a195ca75be81235dc53 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[c:5]):[c:4] | 80 | [{"value": 80.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 6-bromoindole (5.0 g, 26 mmol) in dry DMF (45 mL) was cooled in an ice bath. Sodium hydride (2.2 g of 60% dispersion in oil, 55 mmol) was added. After stirring for 30 minutes under nitrogen at room temperature, the reaction mixture was cooled in an ice bath, and benzyl bromide (6.1 mL, 51 mmol) was added.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | HBr | O.CN(C)C=O | null | 0.5 | BrCc1ccccc1.Brc1ccc2cc[nH]c2c1>O.CN(C)C=O>Brc1ccc2ccn(Cc3ccccc3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-342ffd4e8eef42b181c46cbcb22ed750 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12 | C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O.[OH-].[K+].Cl>>C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18](-[c:19]3[cH:20][cH:21][c:22]([O:23][C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]3)[cH:30][cH:31][c:32]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 82.4 | [{"value": 82.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | A mixture of ethyl 2-[1-benzyl-6-(4-trifluoromethoxyphenyl)-1H-indol-3-yl]-2-oxoacetate (1.27 g, 2.72 mmol), potassium hydroxide (0.539 g, 9.61 mmol) in THF (12 mL) and water (12 mL) was stirred at room temperature for 3.5 hours. The mixture was poured into excess water, acidified with 2N hydrochloric acid, and extract... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2cc[nH]c2c1.c1ccccc1 | Other | O.C1CCOC1 | null | 3.5 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccc(OC(F)(F)F)cc3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-533f120007a64f69984367c0e3cf7c2d | Brc1ccc2ccn(Cc3ccccc3)c2c1.OB(O)c1ccc(C(F)(F)F)cc1>>FC(F)(F)c1ccc(-c2ccc3ccn(Cc4ccccc4)c3c2)cc1 | C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)Br.C([O-])([O-])=O.[Na+].[Na+].FC(C1=CC=C(C=C1)B(O)O)(F)F>>C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=C(C=C1)C(F)(F)F | Br[c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][n:15]([CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]2[cH:24]1.OB(O)[c:8]1[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:26][cH:25]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[cH:13][cH:14][n:15]([CH2:16][c:17]4[cH:18][cH:19][cH:2... | Brc1ccc2ccn(Cc3ccccc3)c2c1.OB(O)c1ccc(C(F)(F)F)cc1 | FC(F)(F)c1ccc(-c2ccc3ccn(Cc4ccccc4)c3c2)cc1 | 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.C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | e5ead5b904b0190a128418d7442173388e9e1f8d91c97a5f7a23f024c91c663c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[c:6]:1):[#7;a:7](-[C:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:6]:1 | 71 | [{"value": 71.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.9, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Step 2 of Example 5, 1-benzyl-6-bromo-1H-indole (0.490 g, 1.71 mmol), was coupled to 4-trifluoromethylbenzeneboronic acid (0.376 g, 1.98 mmol), using tetrakis(triphenylphosphine)palladium (0.0663 g, 0.057 mmol) and sodium carbonate (0.733 g, 6.92 mmol) in water (3.5 mL), ethanol (2 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccccc1.c1ccc2cc[nH]c2c1 | c1ccccc1.c1ccc2cc[nH]c2c1.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.O.C1(=CC=CC=C1)C.C(C)O | null | null | Brc1ccc2ccn(Cc3ccccc3)c2c1.OB(O)c1ccc(C(F)(F)F)cc1>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.C1(=CC=CC=C1)C.C(C)O>FC(F)(F)c1ccc(-c2ccc3ccn(Cc4ccccc4)c3c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-30913ca1a2fb424e9d5481875641baa2 | CCO.FC(F)(F)c1ccc(-c2ccc3ccn(Cc4ccccc4)c3c2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccc(C(F)(F)F)cc3)ccc12 | C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=C(C=C1)C(F)(F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)C(F)(F)F)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]3)[cH:31][cH:32][c:33]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11][c:12... | CCO.FC(F)(F)c1ccc(-c2ccc3ccn(Cc4ccccc4)c3c2)cc1.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccc(C(F)(F)F)cc3)ccc12 | null | null | null | C-C Coupling | OtherReaction | 34ba1cef5b600f2468b9a4fe43ff5669afe09e6688a408ea8eae10e83b03a2fa | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 62 | [{"value": 62.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)C(F)(F)F)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Step 3 of Example 1, ethyl 2-[1-benzyl-6-(4-trifluoromethyl)-1H-indol-3-yl]-2-oxoacetate was prepared from 1-benzyl-6-[4-(trifluoromethyl)phenyl]-1H-indole (0.392 g, 1.12 mmol), oxalyl chloride (0.11 mL, 1.2 mmol), and ethanol (1.4 mL). Purification by flash chromatography using 5-1... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccccc1.c1ccc2cc[nH]c2c1.c1ccccc1 | HCl | null | null | null | CCO.FC(F)(F)c1ccc(-c2ccc3ccn(Cc4ccccc4)c3c2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccc(C(F)(F)F)cc3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a864c9c08e5647ed97b84d93553ff09c | CC(C)(C)c1ccc(Cn2ccc3ccc(Br)cc32)cc1.OB(O)c1ccc(C(F)(F)F)cc1>>CC(C)(C)c1ccc(Cn2ccc3ccc(-c4ccc(C(F)(F)F)cc4)cc32)cc1 | BrC1=CC=C2C=CN(C2=C1)CC1=CC=C(C=C1)C(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].FC(C1=CC=C(C=C1)B(O)O)(F)F>>C(C)(C)(C)C1=CC=C(CN2C=CC3=CC=C(C=C23)C2=CC=C(C=C2)C(F)(F)F)C=C1 | Br[c:16]1[cH:15][cH:14][c:13]2[cH:12][cH:11][n:10]([CH2:9][c:8]3[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:30][cH:29]3)[c:28]2[cH:27]1.OB(O)[c:17]1[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[cH:14]... | CC(C)(C)c1ccc(Cn2ccc3ccc(Br)cc32)cc1.OB(O)c1ccc(C(F)(F)F)cc1 | CC(C)(C)c1ccc(Cn2ccc3ccc(-c4ccc(C(F)(F)F)cc4)cc32)cc1 | 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.C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | e5ead5b904b0190a128418d7442173388e9e1f8d91c97a5f7a23f024c91c663c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[c:6]:1):[#7;a:7](-[C:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:6]:1 | 67.3 | [{"value": 67.0, "product": "C(C)(C)(C)C1=CC=C(CN2C=CC3=CC=C(C=C23)C2=CC=C(C=C2)C(F)(F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "C(C)(C)(C)C1=CC=C(CN2C=CC3=CC=C(C=C23)C2=CC=C(C=C2)C(F)(F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Step 2 of Example 5, 6-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (0.490 g, 1.43 mmol) was coupled to 4-trifluoromethylbenzeneboronic acid (0.300 g, 1.58 mmol), using tetrakis(triphenylphosphine)palladium (0.0560 g, 0.0484 mmol) and sodium carbonate (0.615 g, 5.80 mmol) in water (2.8 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccccc1.c1ccc2cc[nH]c2c1.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.O.C1(=CC=CC=C1)C.C(C)O | null | null | CC(C)(C)c1ccc(Cn2ccc3ccc(Br)cc32)cc1.OB(O)c1ccc(C(F)(F)F)cc1>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.C1(=CC=CC=C1)C.C(C)O>CC(C)(C)c1ccc(Cn2ccc3ccc(-c4ccc(C(F)(F)F)cc4)cc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-82f766cf4b064edabb6c3152a71bc9eb | CC(C)(C)c1ccc(Cn2ccc3ccc(Br)cc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>CC(C)(C)c1ccc(Cn2ccc3ccc(-c4ccc(OC(F)(F)F)cc4)cc32)cc1 | BrC1=CC=C2C=CN(C2=C1)CC1=CC=C(C=C1)C(C)(C)C.C([O-])([O-])=O.[Na+].[Na+].FC(OC1=CC=C(C=C1)B(O)O)(F)F>>C(C)(C)(C)C1=CC=C(CN2C=CC3=CC=C(C=C23)C2=CC=C(C=C2)OC(F)(F)F)C=C1 | Br[c:16]1[cH:15][cH:14][c:13]2[cH:12][cH:11][n:10]([CH2:9][c:8]3[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:31][cH:30]3)[c:29]2[cH:28]1.OB(O)[c:17]1[cH:18][cH:19][c:20]([O:21][C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[... | CC(C)(C)c1ccc(Cn2ccc3ccc(Br)cc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1 | CC(C)(C)c1ccc(Cn2ccc3ccc(-c4ccc(OC(F)(F)F)cc4)cc32)cc1 | 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.C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | e5ead5b904b0190a128418d7442173388e9e1f8d91c97a5f7a23f024c91c663c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[c:6]:1):[#7;a:7](-[C:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:6]:1 | 61.4 | [{"value": 61.0, "product": "C(C)(C)(C)C1=CC=C(CN2C=CC3=CC=C(C=C23)C2=CC=C(C=C2)OC(F)(F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.4, "product": "C(C)(C)(C)C1=CC=C(CN2C=CC3=CC=C(C=C23)C2=CC=C(C=C2)OC(F)(F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Step 2 of Example 5, 6-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (0.488 g, 1.43 mmol) was coupled to 4-trifluoromethoxybenzene boronic acid (0.329 g, 1.60 mmol), using tetrakis(triphenylphosphine)palladium (0.0574 g, 0.0496 mmol) and sodium carbonate (0.617 g, 5.82 mmol) in water (2.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccccc1.c1ccc2cc[nH]c2c1.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.O.C1(=CC=CC=C1)C.C(C)O | null | null | CC(C)(C)c1ccc(Cn2ccc3ccc(Br)cc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>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.C1(=CC=CC=C1)C.C(C)O>CC(C)(C)c1ccc(Cn2ccc3ccc(-c4ccc(OC(F)(F)F)cc4)cc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b034a95717e94faaaded207b834788aa | BrCc1ccccc1.Brc1ccc2[nH]ccc2c1>>Brc1ccc2c(ccn2Cc2ccccc2)c1 | BrC=1C=C2C=CNC2=CC1.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br | Br[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][nH:9]2)[cH:17]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][n:9]2[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1 | BrCc1ccccc1.Brc1ccc2[nH]ccc2c1 | Brc1ccc2c(ccn2Cc2ccccc2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[c:5]):[c:4] | 78 | [{"value": 78.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 5-bromoindole (5.02 g, 25.6 mmol) and benzyl bromide (6.7 mL, 56 mmol), following the procedure described in Step 1 of Example 5. Purification by flash chromatography on Biotage apparatus using hexane as an eluant yielded 1-benzyl-5-bromo-1H-indole as a white solid (5.69 g, 78%), mp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | null | null | null | BrCc1ccccc1.Brc1ccc2[nH]ccc2c1>>Brc1ccc2c(ccn2Cc2ccccc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2634fc9878574c259590b03776e602df | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccc(C(F)(F)F)cc1>>FC(F)(F)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)C.FC(C1=CC=C(C=C1)B(O)O)(F)F>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(F)(F)F | Br[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14][cH:15][n:16]2[CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24]1.OB(O)[c:8]1[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:26][cH:25]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14][cH:15][n:16]3[CH2:17][c:18]3[cH:19][cH:2... | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccc(C(F)(F)F)cc1 | FC(F)(F)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 | 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.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 12 | [{"value": 12.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.6, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Step 2 of Example 5 1-benzyl-5-bromo-1H-indole (2.22 g , 7.76 mmol) was coupled to 4-trifluoromethylphenyl boronic acid (1.62 g, 8.54 mmol), using tetrakis(triphenylphosphine)palladium (0.892 g, 0.772 mmol), and potassium carbonate (4.29 g, 31.1 mmol) in water (17 mL), ethanol (4 mL... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.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.O.C(C)O | null | null | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccc(C(F)(F)F)cc1>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.C(C)O>FC(F)(F)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e01a895d7f2741e6b99848f3311dc8ad | CCO.FC(F)(F)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(F)(F)F)cc3)cc12 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(F)(F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(F)(F)F)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]3)[cH:32][c:33]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11][c:12... | CCO.FC(F)(F)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(F)(F)F)cc3)cc12 | null | null | null | C-C Coupling | OtherReaction | e42beb79999369525e781f5f2a8c25a764f237d2f2302bca9902d8152413d7f2 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 63 | [{"value": 63.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl 2-{1-benzyl-5-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetate was prepared from 1-Benzyl-5-[4-(trifluoromethyl)phenyl]-1H-indole (0.307 g, 0.874 mmol), oxalyl chloride (0.29 mL, 3.3 mmol), and ethanol (3 mL) following the procedure described in Step 3 of Example 1. The compound was purified by flash chrom... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | null | null | null | CCO.FC(F)(F)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(F)(F)F)cc3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c2e26f6f493b4bb48f6f3a1bd322f44d | CC(C)(C)c1ccc(B(O)O)cc1.Cn1ccc2ccc(Br)cc21>>Cn1ccc2ccc(-c3ccc(C(C)(C)C)cc3)cc21 | BrC1=CC=C2C=CN(C2=C1)C.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)C.C(C)(C)(C)C1=CC=C(C=C1)B(O)O>>C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C | OB(O)[c:9]1[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]1.Br[c:8]1[cH:7][cH:6][c:5]2[cH:4][cH:3][n:2]([CH3:1])[c:20]2[cH:19]1>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]3)[cH:19][c:20]12 | CC(C)(C)c1ccc(B(O)O)cc1.Cn1ccc2ccc(Br)cc21 | Cn1ccc2ccc(-c3ccc(C(C)(C)C)cc3)cc21 | 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.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | e5ead5b904b0190a128418d7442173388e9e1f8d91c97a5f7a23f024c91c663c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:6]:[c:5]:[c:4]:1 | 56.3 | [{"value": 56.0, "product": "C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure described in Step 2 of Example 5, 6-bromo-1-methyl-1H-indole (1.12 g , 5.33 mmol) was coupled to 4-(tert-butyl)phenylboronic acid (1.07 g, 6.00 mmol), using tetrakis(triphenylphosphine)palladium (0.655 g, 0.567 mmol), and potassium carbonate (2.94 g, 21.3 mmol) in water (10.6 mL), ethanol (2.2 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.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.O.C(C)O | null | null | CC(C)(C)c1ccc(B(O)O)cc1.Cn1ccc2ccc(Br)cc21>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.C(C)O>Cn1ccc2ccc(-c3ccc(C(C)(C)C)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4747b25811be4a4e9fc257ce77068864 | CCO.Cn1ccc2ccc(-c3ccc(C(C)(C)C)cc3)cc21.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(C)c2cc(-c3ccc(C(C)(C)C)cc3)ccc12 | C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C2C(=CN(C2=C1)C)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH3:11])[c:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]3)[cH:25][cH:26][c:27]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH3:11])[c:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:1... | CCO.Cn1ccc2ccc(-c3ccc(C(C)(C)C)cc3)cc21.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(C)c2cc(-c3ccc(C(C)(C)C)cc3)ccc12 | null | null | null | C-C Coupling | OtherReaction | 34ba1cef5b600f2468b9a4fe43ff5669afe09e6688a408ea8eae10e83b03a2fa | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[C:14]-[OH;D1;+0:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:15]-[C:14]-[C;D1;H3:13]):[c:9](:[c:... | 44 | [{"value": 44.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl 2-{6-[4-(tert-butyl)phenyl]-1-methyl-1H-indol-3-yl}-2-oxoacetate was prepared from 6-[4-(tert-butyl)phenyl]-1-methyl-1H-indole (0.230 g, 0.874 mmol), oxalyl chloride (0.16 mL, 1.8 mmol), and ethanol (2 mL) following the procedure described in Step 3 of Example 1. The compound was purified by HPLC using 30% ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | HCl | null | null | null | CCO.Cn1ccc2ccc(-c3ccc(C(C)(C)C)cc3)cc21.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(C)c2cc(-c3ccc(C(C)(C)C)cc3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-add1bbb702764cd4aefffe78fcdf3eb4 | Brc1ccc2c(ccn2Cc2ccccc2)c1.CC(=O)c1ccc(B(O)O)cc1>>CC(=O)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br.C(C)(=O)C1=CC=C(C=C1)B(O)O.ClCCl.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(C)=O | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13][cH:14][n:15]2[CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1.OB(O)[c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:25][cH:24]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13][cH:14][n:15]3[CH2:16][c:17]3[cH:18][cH:19][cH:20][... | Brc1ccc2c(ccn2Cc2ccccc2)c1.CC(=O)c1ccc(B(O)O)cc1 | CC(=O)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:6]:[c:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3]:1 | 23.1 | [{"value": 23.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.1, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 67.5 | CELSIUS | null | null | A mixture of 1-benzyl-5-bromo-1H-indole (1.00 g, 3.49 mmol), 4-acetylphenylboronic acid (0.692 g, 4.22 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.0581 g, 0.0711 mmol), potassium carbonate (0.725 g, 5.25 mmol) in dioxane (35 mL) and water (3.5 mL) was heated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O | 67.5 | null | Brc1ccc2c(ccn2Cc2ccccc2)c1.CC(=O)c1ccc(B(O)O)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O>CC(=O)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6f7e945e1c1e487487f9c21e4512dfe5 | CC(=O)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.CCO.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)=O)cc3)cc12 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(C)=O.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C)(=O)C1=CC=C(C=C1)C=1C=C2C(=CN(C2=CC1)CC1=CC=CC=C1)C(C(=O)OCC)=O | [cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][cH:24][c:25]([C:26]([CH3:27])=[O:28])[cH:29][cH:30]3)[cH:31][c:32]12.[CH3:1][CH2:2][OH:3].Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11][c:12]2[cH... | CC(=O)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.CCO.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)=O)cc3)cc12 | null | null | null | C-C Coupling | OtherReaction | e42beb79999369525e781f5f2a8c25a764f237d2f2302bca9902d8152413d7f2 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 73 | [{"value": 73.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl 2-[5-(4-acetylphenyl)-1-benzyl-1H-indol-3-yl]-2-oxoacetate was prepared from 1-[4-(1-benzyl-1H-indol-5-yl)phenyl]-1-ethanone (0.255 g, 0.784 mmol), oxalyl chloride (0.14 mL, 1.6 mmol), and ethanol (2 mL), following the procedure described in Step 3 of Example 1. Purification by flash chromatography using 30-50% c... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | null | null | null | CC(=O)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.CCO.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)=O)cc3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-90ba35bbb5744071ba40ae18809bfa2a | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)=O)cc3)cc12>>CC(=O)c1ccc(-c2ccc3c(c2)c(C(=O)C(=O)O)cn3Cc2ccccc2)cc1 | C(C)(=O)C1=CC=C(C=C1)C=1C=C2C(=CN(C2=CC1)CC1=CC=CC=C1)C(C(=O)OCC)=O.[OH-].[K+]>>C(C)(=O)C1=CC=C(C=C1)C=1C=C2C(=CN(C2=CC1)CC1=CC=CC=C1)C(C(=O)O)=O | CC[O:19][C:17]([C:15]([c:14]1[c:12]2[c:11]([cH:10][cH:9][c:8](-[c:7]3[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:30][cH:29]3)[cH:13]2)[n:21]([CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:20]1)=[O:16])=[O:18]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[c:14]([C:15](=... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)=O)cc3)cc12 | CC(=O)c1ccc(-c2ccc3c(c2)c(C(=O)C(=O)O)cn3Cc2ccccc2)cc1 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 79 | [{"value": 79.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | [5-(4-Acetylphenyl)-1-benzyl-1H-indol-3-yl](oxo)acetic acid was prepared from ethyl [5-(4-acetylphenyl)-1-benzyl-1H-indol-3-yl](oxo)acetate (0.225 g, 0.529 mmol), and potassium hydroxide (0.104 g, 1.85 mmol) in THF (7 mL) and water (7 mL) according to the procedure described in Step 4 of Example 5. After drying for 15 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)=O)cc3)cc12>O.C1CCOC1>CC(=O)c1ccc(-c2ccc3c(c2)c(C(=O)C(=O)O)cn3Cc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b000ba4fdadf48c88fba2e3eb29df2a7 | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccc(OC(F)(F)F)cc1>>FC(F)(F)Oc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 | C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br.FC(OC1=CC=C(C=C1)B(O)O)(F)F.ClCCl>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F | Br[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15][cH:16][n:17]2[CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25]1.OB(O)[c:9]1[cH:8][cH:7][c:6]([O:5][C:2]([F:1])([F:3])[F:4])[cH:27][cH:26]1>>[F:1][C:2]([F:3])([F:4])[O:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15][cH:16][n:17]3[CH2:18][c:19]3... | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccc(OC(F)(F)F)cc1 | FC(F)(F)Oc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 | null | null | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 42.3 | [{"value": 42.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.3, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indole was prepared by coupling of 1-benzyl-5-bromo-1H-indole (5.2 g, 18 mmol) and 4-trifluoromethoxyphenylboronic acid (4.7 g, 23 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.88 g, 1.1 mmol), and potassium carb... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | O1CCOCC1.O | null | null | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccc(OC(F)(F)F)cc1>O1CCOCC1.O>FC(F)(F)Oc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-beb8c372c1874d9dbd1a35d0b89ab607 | CCO.FC(F)(F)Oc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][cH:24][c:25]([O:26][C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]3)[cH:33][c:34]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11... | CCO.FC(F)(F)Oc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 | null | null | null | C-C Coupling | OtherReaction | e42beb79999369525e781f5f2a8c25a764f237d2f2302bca9902d8152413d7f2 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 86 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl {1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indole (2.80 g, 7.62 mmol), oxalyl chloride (2.0 mL, 23 mmol), and ethanol (4.5 mL) according to the procedure described in Step 3 of Example 1. Purification by flash chromatography usi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | null | null | null | CCO.FC(F)(F)Oc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-530540b8c0fc469a9d1be021f158d7b2 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 | C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]3)[cH:31][c:32]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 78 | [{"value": 78.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | {1-Benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl 2-{1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}-2-oxoacetate (0.463 g, 0.991 mmol), potassium hydroxide (0.224 g, 3.99 mmol) in THF (5 mL) and water (5 mL) according to the procedure described in Step 4 of Example ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff17ac096ed14b599432d70caad2a867 | BrCc1ccccc1.Brc1cccc2[nH]ccc12>>Brc1cccc2c1ccn2Cc1ccccc1 | BrC1=C2C=CNC2=CC=C1.[H-].[Na+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)Br | Br[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][cH:9][nH:10]2>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][cH:9][n:10]2[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | BrCc1ccccc1.Brc1cccc2[nH]ccc12 | Brc1cccc2c1ccn2Cc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 558bcff26233c13696ebcbebe920e2039c7ee6d2503304edb672d21289ef564c | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[c:5]):[c:4] | 70 | [{"value": 70.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-4-bromo-1H-indole was prepared from 4-bromo-1H-indole (1.58 g, 8.06 mmol), sodium hydride (0.680 g of 60% dispersion in oil, 17.0 mmol), and benzyl bromide (2.0 mL, 17 mmol) in DMF (15 mL) according to the procedure described in Step 1 of Example 5. Purification by flash chromatography (Biotage apparatus) usin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12.c1ccccc1 | HBr | CN(C)C=O | null | null | BrCc1ccccc1.Brc1cccc2[nH]ccc12>CN(C)C=O>Brc1cccc2c1ccn2Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5eadb8a6a78948e199d1864736a5eee0 | Brc1cccc2c1ccn2Cc1ccccc1.OB(O)c1ccc(C(F)(F)F)cc1>>FC(F)(F)c1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1 | C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)Br.FC(C1=CC=C(C=C1)B(O)O)(F)F.ClCCl>>C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F | Br[c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[cH:15][cH:16][n:17]2[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.OB(O)[c:8]1[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:26][cH:25]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[c:14]2[cH:15][cH:16][n:17]3[CH2:18][c:19]2[cH:20]... | Brc1cccc2c1ccn2Cc1ccccc1.OB(O)c1ccc(C(F)(F)F)cc1 | FC(F)(F)c1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | fbb3b8648e869cd93c2731d6a9721a7097442302f467cc4cb1d3d6bf3de6e845 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3c(-c4ccccc4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[c:9]:[c:10]:2:1.O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C:7]-[#7;a:6]1:[c:8]:[c:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15] | 49.1 | [{"value": 49.0, "product": "C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.1, "product": "C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indole was prepared by coupling of 1-benzyl-4-bromo-1H-indole (0.428 g, 1.50 mmol), and 4-trifluoromethylphenylboronic acid (0.374 g, 1.97 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.0638 g, 0.0781 mmol), and p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cccc2[nH]ccc12.c1ccccc1 | c1ccccc1.c1cccc2[nH]ccc12 | c1ccccc1.c1cccc2[nH]ccc12.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O | null | null | Brc1cccc2c1ccn2Cc1ccccc1.OB(O)c1ccc(C(F)(F)F)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O>FC(F)(F)c1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7c980a79f7864a7aba53e17c86104c1e | CCO.FC(F)(F)c1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(C(F)(F)F)cc3)c12 | C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]3)[c:33]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11][c:12... | CCO.FC(F)(F)c1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(C(F)(F)F)cc3)c12 | null | null | null | C-C Coupling | OtherReaction | 5793860a02afd332539e048290c7a2c0198114fbd04f124edb77c013e70ddad9 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3c(-c4ccccc4)cccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 19 | [{"value": 19.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl {1-benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indole (0.257 g, 0.731 mmol), oxalyl chloride (2.2 mL, 26 mmol), and ethanol (6 mL) according to the procedure described in Step 3 of Example 1. Purification by HPLC using 3% ethanol in h... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12 | c1ccccc1.c1cccc2[nH]ccc12.c1ccccc1 | HCl | null | null | null | CCO.FC(F)(F)c1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(C(F)(F)F)cc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c79f09fc79c7444c97786333fbdb8cf4 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(C(F)(F)F)cc3)c12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(C(F)(F)F)cc3)c12 | C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)C(F)(F)F)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]3)[c:31]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(C(F)(F)F)cc3)c12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(C(F)(F)F)cc3)c12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3c(-c4ccccc4)cccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 89 | [{"value": 89.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-{1-Benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetic acid was prepared from ethyl {1-benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl}(oxo)acetate (0.064 g, 0.142 mmol), and potassium hydroxide (0.0471 g, 0.839 mmol) in THF (2.5 mL) and water (2.5 mL) according to the procedure described in Step 4 of ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cccc2[nH]ccc12.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(C(F)(F)F)cc3)c12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(C(F)(F)F)cc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a5590bbaca1c49449801de188a82774f | Brc1ccc2c(ccn2Cc2ccccc2)c1.CC(C)(C)c1ccc(B(O)O)cc1>>CC(C)(C)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 | ClCCl.C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br.C([O-])([O-])=O.[K+].[K+].C(C)(C)(C)C1=CC=C(C=C1)B(O)O>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(C)(C)C | Br[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14][cH:15][n:16]2[CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24]1.OB(O)[c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:26][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14][cH:15][n:16]3[CH2:17][c:18]3... | Brc1ccc2c(ccn2Cc2ccccc2)c1.CC(C)(C)c1ccc(B(O)O)cc1 | CC(C)(C)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 | null | null | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 43 | [{"value": 43.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | -Benzyl-5-[4-(tert-butyl)phenyl]-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (1.44 g, 5.03 mmol), and 4-(tert-butyl)phenylboronic acid (1.08 g, 6.07 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.204 g, 0.250 mmol), and potassium carbonat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | O1CCOCC1.O | null | null | Brc1ccc2c(ccn2Cc2ccccc2)c1.CC(C)(C)c1ccc(B(O)O)cc1>O1CCOCC1.O>CC(C)(C)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7346e97b0d534059ab16adae8773d442 | CC(C)(C)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.CCO.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)(C)C)cc3)cc12 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(C)(C)C.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C(C(=O)OCC)=O | [cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][cH:24][c:25]([C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30][cH:31]3)[cH:32][c:33]12.[CH3:1][CH2:2][OH:3].Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11... | CC(C)(C)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.CCO.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)(C)C)cc3)cc12 | null | null | null | C-C Coupling | OtherReaction | e42beb79999369525e781f5f2a8c25a764f237d2f2302bca9902d8152413d7f2 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 71 | [{"value": 71.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl {1-benzyl-5-[4-(tert-butyl)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-5-[4-(tert-butyl)phenyl]-1H-indole (0.732 g, 2.16 mmol), oxalyl chloride (0.75 mL, 8.6 mmol), and ethanol (6 mL) according to the procedure described in Step 3 of Example 1. Purification by flash chromatography (Biotage appar... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | null | null | null | CC(C)(C)c1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1.CCO.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)(C)C)cc3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8535b288aabf478793bc4f72dd9269a4 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)(C)C)cc3)cc12>>CC(C)(C)c1ccc(-c2ccc3c(c2)c(C(=O)C(=O)O)cn3Cc2ccccc2)cc1 | C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C(C(=O)O)=O | CC[O:20][C:18]([C:16]([c:15]1[c:13]2[c:12]([cH:11][cH:10][c:9](-[c:8]3[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:31][cH:30]3)[cH:14]2)[n:22]([CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[cH:21]1)=[O:17])=[O:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([c... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)(C)C)cc3)cc12 | CC(C)(C)c1ccc(-c2ccc3c(c2)c(C(=O)C(=O)O)cn3Cc2ccccc2)cc1 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 63 | [{"value": 63.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.5, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | {1-Benzyl-5-[4-(tert-butyl)phenyl]-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-benzyl-5-[4-(tert-butyl)phenyl]-1H-indol-3-yl}(oxo)acetate (0.669 g, 1.52 mmol), potassium hydroxide (0.30 g, 5.3 mmol) in THF (15 mL) and water (15 mL) according to the procedure described in Step 4 of Example 5. Purification ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(C(C)(C)C)cc3)cc12>O.C1CCOC1>CC(C)(C)c1ccc(-c2ccc3c(c2)c(C(=O)C(=O)O)cn3Cc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-55831a8369d64bbb840cf0be7b69fe58 | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccc(F)c(Cl)c1>>Fc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1Cl | C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br.ClC=1C=C(C=CC1F)B(O)O.ClCCl>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl | Br[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11][cH:12][n:13]2[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21]1.OB(O)[c:5]1[cH:4][cH:3][c:2]([F:1])[c:23]([Cl:24])[cH:22]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11][cH:12][n:13]3[CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21]2)[c... | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccc(F)c(Cl)c1 | Fc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1Cl | null | null | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 41.2 | [{"value": 41.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.2, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-5-(3-chloro-4-fluorophenyl)-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (1.46 g, 5.10 mmol), and 3-chloro-4-fluorophenylboronic acid (1.08 g, 6.19 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (0.209 g, 0.256 mmol), potassium carbonate (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | O1CCOCC1.O | null | null | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccc(F)c(Cl)c1>O1CCOCC1.O>Fc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d8784c002a74cf8bc3846c4cbf591f2 | CCO.Fc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1Cl.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][cH:24][c:25]([F:26])[c:27]([Cl:28])[cH:29]3)[cH:30][c:31]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:1... | CCO.Fc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1Cl.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 | null | null | null | C-C Coupling | OtherReaction | e42beb79999369525e781f5f2a8c25a764f237d2f2302bca9902d8152413d7f2 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 67 | [{"value": 67.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl [1-benzyl-5-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetate was prepared from 1-benzyl-5-(3-chloro-4-fluorophenyl)-1H-indole (0.705 g, 2.10 mmol), oxalyl chloride (0.73 mL, 8.4 mmol), and ethanol (6 mL) according to the procedure described in Step 3 of Example 1. Purification by flash chromatography (Biotage... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | null | null | null | CCO.Fc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1Cl.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9684be9b769745cbb068c64cd21cf469 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 | C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([F:24])[c:25]([Cl:26])[cH:27]3)[cH:28][c:29]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:1... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 63.1 | [{"value": 63.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.1, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | [1-Benzyl-5-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetic acid was prepared from ethyl [1-benzyl-5-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetate (0.540 g, 1.24 mmol), and potassium hydroxide (0.218 g, 3.89 mmol) in THF (6 mL) and water (6 mL) according to the procedure described in Step 4 of Example 5. Pur... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9efed3bbc98145168136c10b10774f1f | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>FC(F)(F)c1cc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc(C(F)(F)F)c1 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br.ClCCl.C([O-])([O-])=O.[K+].[K+].FC(C=1C=C(C=C(C1)C(F)(F)F)B(O)O)(F)F>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13][cH:14][n:15]2[CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23]1.OB(O)[c:7]1[cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:30][c:25]([C:26]([F:27])([F:28])[F:29])[cH:24]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13][cH:14][n:15]3[CH2:... | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | FC(F)(F)c1cc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc(C(F)(F)F)c1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:6]:[c:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3]:1 | 51.2 | [{"value": 51.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.2, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | 1-Benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (1.44 g, 5.03 mmol), and 3,5-bis-(trifluoromethyl)phenylboronic acid (1.63 g, 6.32 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.211 g, 0.258 mmol),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O | 85 | null | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O>FC(F)(F)c1cc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-174825499dbe47fc9e22acd8c0a18a7f | CCO.FC(F)(F)c1cc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc(C(F)(F)F)c1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cc12 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]3)[cH:36][c:37]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:... | CCO.FC(F)(F)c1cc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc(C(F)(F)F)c1.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cc12 | null | null | null | C-C Coupling | OtherReaction | e42beb79999369525e781f5f2a8c25a764f237d2f2302bca9902d8152413d7f2 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 56 | [{"value": 56.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl 2-{1-benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indol-3-yl}-2-oxoacetate was prepared from 1-benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indole (1.07 g, 2.56 mmol), oxalyl chloride (1.3 mL, 15 mmol), and ethanol (6 mL) following the procedure described in Step 3 of Example 1. Purification by HPLC (reverse phas... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | null | null | null | CCO.FC(F)(F)c1cc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc(C(F)(F)F)c1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2abd0341df1244ccbb6b0996076dfb3a | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cc12 | C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33]3)[cH:34][c:35]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 47 | [{"value": 47.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.7, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | null | null | {1-Benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indol-3-yl}(oxo)acetate (0.737 g, 1.42 mmol), potassium hydroxide (0.260 g, 4.63 mmol) in THF (9 mL) and water (9 mL) according to the procedure described in Step 4 of Exam... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cc(C(F)(F)F)cc(C(F)(F)F)c3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-195acbbe1c964c13a624ceaf3d90c5c7 | BrCc1ccccc1.Brc1cccc2cc[nH]c12>>Brc1cccc2ccn(Cc3ccccc3)c12 | C(C1=CC=CC=C1)Br.[H-].[Na+].BrC=1C=CC=C2C=CNC12.[H-].[Na+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)Br | Br[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][nH:9][c:17]12>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][n:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]12 | BrCc1ccccc1.Brc1cccc2cc[nH]c12 | Brc1cccc2ccn(Cc3ccccc3)c12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2aaeeb108110653b7344d63d8c91a47829603f83b5ee630834fbd27b41092371 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[c:5]):[c:4] | 70 | [{"value": 70.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1-Benzyl-7-bromo-1H-indole was prepared from 7-bromo-1H-indole (0.500 g, 2.55 mmol), sodium hydride (0.285 g, 7.13 mmol of 60% dispersion on mineral oil), benzyl bromide (0.67 mL, 5.6 mmol) in DMF (5 mL). The reaction mixture was stirred for 1 hour after the addition of sodium hydride and for 1 hour after the addition ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cccc2cc[nH]c12 | c1cccc2cc[nH]c12.c1ccccc1 | HBr | CN(C)C=O | null | 1 | BrCc1ccccc1.Brc1cccc2cc[nH]c12>CN(C)C=O>Brc1cccc2ccn(Cc3ccccc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-384b85ce88b143f395cd517ddf4a9ccf | Brc1cccc2ccn(Cc3ccccc3)c12.OB(O)c1ccc(OC(F)(F)F)cc1>>FC(F)(F)Oc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1 | C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)Br.ClCCl.C([O-])([O-])=O.[K+].[K+].FC(OC1=CC=C(C=C1)B(O)O)(F)F>>C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F | Br[c:10]1[cH:11][cH:12][cH:13][c:14]2[cH:15][cH:16][n:17]([CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]12.OB(O)[c:9]1[cH:8][cH:7][c:6]([O:5][C:2]([F:1])([F:3])[F:4])[cH:27][cH:26]1>>[F:1][C:2]([F:3])([F:4])[O:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][c:14]3[cH:15][cH:16][n:17]([CH2:18][c:19]4... | Brc1cccc2ccn(Cc3ccccc3)c12.OB(O)c1ccc(OC(F)(F)F)cc1 | FC(F)(F)Oc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O1CCOCC1.O.CCCCCC | C-C Coupling | Suzuki coupling with boronic acids | 32dc97e8f2e0cf2775d54ef6c7686d3196d1acbccb9916fdeb04e8bbe0354c56 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cccc(-c4ccccc4)c32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6](-[C:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:7]-[#7;a:6](:[c:8]):[c:4](:[c:5]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:2]:[c:3] | 50 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.6, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-7-bromo-1H-indole (0.677 g, 2.37 mmol) was coupled to 4-trifluoromethoxyphenylboronic acid (0.585 g, 2.84 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.0585 g, 0.0716 mmol), and potassium carbonate (0.492 g, 3.56 mmol), in dioxane (18 mL) and wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cccc2cc[nH]c12.c1ccccc1 | c1ccccc1.c1cccc2cc[nH]c12 | c1ccccc1.c1cccc2cc[nH]c12.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O.CCCCCC | null | null | Brc1cccc2ccn(Cc3ccccc3)c12.OB(O)c1ccc(OC(F)(F)F)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O.CCCCCC>FC(F)(F)Oc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5d5641fd4b454eecbcc68e8935391e6e | CCO.FC(F)(F)Oc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(OC(F)(F)F)cc3)cccc12 | C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[c:19](-[c:20]3[cH:21][cH:22][c:23]([O:24][C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]3)[cH:31][cH:32][cH:33][c:34]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11... | CCO.FC(F)(F)Oc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(OC(F)(F)F)cc3)cccc12 | null | null | null | C-C Coupling | OtherReaction | 751b266abfd2a6116754d8ed76996beab018e20bfb67af6bda939c8237363ac9 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cccc(-c4ccccc4)c32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 61 | [{"value": 61.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl {1-benzyl-7-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-7-[4-(trifluoromethoxy)phenyl]-1H-indole (0.421 g, 1.15 mmol), oxalyl chloride (0.60 mL, 6.9 mmol), and ethanol (3 mL) following the procedure described in Step 3 of Example 1. Purification by flash chromatography (Biot... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1cccc2cc[nH]c12 | c1c[nH]c2ccccc12 | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | HCl | null | null | null | CCO.FC(F)(F)Oc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(OC(F)(F)F)cc3)cccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dabaee00127343d8a1c0c258939cb853 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(OC(F)(F)F)cc3)cccc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(OC(F)(F)F)cc3)cccc12 | C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[c:17](-[c:18]3[cH:19][cH:20][c:21]([O:22][C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]3)[cH:29][cH:30][cH:31][c:32]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(OC(F)(F)F)cc3)cccc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(OC(F)(F)F)cc3)cccc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cccc(-c4ccccc4)c32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 57.2 | [{"value": 57.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.2, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | {1-Benzyl-7-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-benzyl-7-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate (0.318 g, 0.680 mmol), and potassium hydroxide (0.123 g, 2.19 mmol) in THF (3 mL) and water (3 mL) according to the procedure described in Step 4 of Example... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(OC(F)(F)F)cc3)cccc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(OC(F)(F)F)cc3)cccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7ecc296cf1241b38026374809e6470c | Brc1cccc2ccn(Cc3ccccc3)c12.OB(O)c1ccc(F)c(Cl)c1>>Fc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1Cl | C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)Br.ClCCl.C([O-])([O-])=O.[K+].[K+].ClC=1C=C(C=CC1F)B(O)O>>C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl | Br[c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][cH:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]12.OB(O)[c:5]1[cH:4][cH:3][c:2]([F:1])[c:23]([Cl:24])[cH:22]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][n:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[c:21]23)[c... | Brc1cccc2ccn(Cc3ccccc3)c12.OB(O)c1ccc(F)c(Cl)c1 | Fc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1Cl | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 32dc97e8f2e0cf2775d54ef6c7686d3196d1acbccb9916fdeb04e8bbe0354c56 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cccc(-c4ccccc4)c32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6](-[C:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:7]-[#7;a:6](:[c:8]):[c:4](:[c:5]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:2]:[c:3] | 23.4 | [{"value": 23.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.4, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-7-(3-chloro-4-fluorophenyl)-1H-indole was prepared by coupling 1-benzyl-7-bromo-1H-indole (0.691 g, 2.41 mmol), and 3-chloro-4-fluorophenylboronic acid (0.538 g, 3.09 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.0628 g, 0.0769 mmol), and potass... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cccc2cc[nH]c12.c1ccccc1 | c1ccccc1.c1cccc2cc[nH]c12 | c1ccccc1.c1cccc2cc[nH]c12.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O | null | null | Brc1cccc2ccn(Cc3ccccc3)c12.OB(O)c1ccc(F)c(Cl)c1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O>Fc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bd863056aa224760b30db0382ce186ce | CCO.Fc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1Cl.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(F)c(Cl)c3)cccc12 | C(C1=CC=CC=C1)N1C=CC2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[c:19](-[c:20]3[cH:21][cH:22][c:23]([F:24])[c:25]([Cl:26])[cH:27]3)[cH:28][cH:29][cH:30][c:31]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:1... | CCO.Fc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1Cl.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(F)c(Cl)c3)cccc12 | null | null | null | C-C Coupling | OtherReaction | 751b266abfd2a6116754d8ed76996beab018e20bfb67af6bda939c8237363ac9 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cccc(-c4ccccc4)c32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 61 | [{"value": 61.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl [1-benzyl-7-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetate was prepared from 1-benzyl-7-(3-chloro-4-fluorophenyl)-1H-indole (0.182 g, 0.542 mmol), oxalyl chloride (0.28 mL, 3.3 mmol), and ethanol (0.75 mL) following the procedure described in Step 3 of Example 1. Purification by HPLC using 20% ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1cccc2cc[nH]c12 | c1c[nH]c2ccccc12 | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | HCl | null | null | null | CCO.Fc1ccc(-c2cccc3ccn(Cc4ccccc4)c23)cc1Cl.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(F)c(Cl)c3)cccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da890bf8f61b420d90b8ed4a73e84f0a | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(F)c(Cl)c3)cccc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(F)c(Cl)c3)cccc12 | C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)OCC)=O.[OH-].[K+].CCCCCC>>C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[c:17](-[c:18]3[cH:19][cH:20][c:21]([F:22])[c:23]([Cl:24])[cH:25]3)[cH:26][cH:27][cH:28][c:29]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[c:17... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(F)c(Cl)c3)cccc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(F)c(Cl)c3)cccc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cccc(-c4ccccc4)c32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 64.3 | [{"value": 64.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.3, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=CC(=C12)C1=CC(=C(C=C1)F)Cl)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | [1-Benzyl-7-(3-chloro-4-fluorophenyl)-1H-indol-3-yl](oxo)acetic acid was prepared from ethyl 2-[1-benzyl-7-(3-chloro-4-fluorophenyl)-1H-indol-3-yl]-2-oxoacetate (0.139 g, 0.319 mmol), and potassium hydroxide (0.076 g, 1.35 mmol) in THF (2.5 mL) and water (2.5 mL) following the procedure described in Step 4 of Example 5... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(F)c(Cl)c3)cccc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2c(-c3ccc(F)c(Cl)c3)cccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f477b765a5214464af79f76c80b7c998 | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)Br)C=C1.ClCCl.C([O-])([O-])=O.[K+].[K+].FC(OC1=CC=C(C=C1)B(O)O)(F)F>>C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C=C1 | Br[c:15]1[cH:14][c:13]2[cH:12][cH:11][n:10]([CH2:9][c:8]3[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:31][cH:30]3)[c:29]2[cH:28][cH:27]1.OB(O)[c:16]1[cH:17][cH:18][c:19]([O:20][C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[... | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1 | CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | null | null | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | 1-[4-(tert-Butyl)benzyl]-5-[4-(trifluoromethoxy)phenyl]-1H-indole was prepared by coupling 1-[4-(tert-Butyl)benzyl]-5-bromo-1H-indole (5.34 g, 15.6 mmol), and 4-trifluoromethoxyphenyl boronic acid (3.86 g, 18.7 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | O1CCOCC1.O | null | null | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>O1CCOCC1.O>CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3119e9a0fb8f43e491e3118e017a24b3 | CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1.CCO.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccc(C(C)(C)C)cc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 | C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C=C1.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C)OC(C(=O)C1=CN(C2=CC=C(C=C12)C1=CC=C(C=C1)OC(F)(F)F)CC1=CC=C(C=C1)C(C)(C)C)=O | [cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][c:25](-[c:26]3[cH:27][cH:28][c:29]([O:30][C:31]([F:32])([F:33])[F:34])[cH:35][cH:36]3)[cH:37][c:38]12.[CH3:1][CH2:2][OH:3].Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6... | CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1.CCO.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccc(C(C)(C)C)cc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 | null | null | null | C-C Coupling | OtherReaction | e42beb79999369525e781f5f2a8c25a764f237d2f2302bca9902d8152413d7f2 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 59 | [{"value": 59.0, "product": "C(C)OC(C(=O)C1=CN(C2=CC=C(C=C12)C1=CC=C(C=C1)OC(F)(F)F)CC1=CC=C(C=C1)C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl {1-[4-(tert-butyl)benzyl]-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-[4-(tert-butyl)benzyl]-5-[4-(trifluoromethoxy)phenyl]-1H-indole (2.52 g, 5.95 mmol), oxalyl chloride (1.6 mL, 18 mmol), and ethanol (5 mL) following the procedure described in Step 3 of Example 1. Purification ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | null | null | null | CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1.CCO.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccc(C(C)(C)C)cc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93121ab036ab4668969dbb9462ec688e | CCOC(=O)C(=O)c1cn(Cc2ccc(C(C)(C)C)cc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12>>CC(C)(C)c1ccc(Cn2cc(C(=O)C(=O)O)c3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | C(C)(C)(C)C1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C(C(=O)OCC)=O)C=C1.[OH-].[K+].CCCCCC>>C(C)(C)(C)C1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C(C(=O)O)=O)C=C1 | CC[O:17][C:15]([C:13]([c:12]1[cH:11][n:10]([CH2:9][c:8]2[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:36][cH:35]2)[c:34]2[c:18]1[cH:19][c:20](-[c:21]1[cH:22][cH:23][c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]1)[cH:32][cH:33]2)=[O:14])=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2... | CCOC(=O)C(=O)c1cn(Cc2ccc(C(C)(C)C)cc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12 | CC(C)(C)c1ccc(Cn2cc(C(=O)C(=O)O)c3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 69 | [{"value": 69.0, "product": "C(C)(C)(C)C1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C(C(=O)O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.7, "product": "C(C)(C)(C)C1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C(C(=O)O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | {1-[4-(tert-Butyl)benzyl]-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-[4-(tert-butyl)benzyl]-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate (1.72 g, 3.29 mmol), and potassium hydroxide (0.614 g, 10.9 mmol) in THF (20 mL) and water (20 mL) following the procedure d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccc(C(C)(C)C)cc2)c2ccc(-c3ccc(OC(F)(F)F)cc3)cc12>O.C1CCOC1>CC(C)(C)c1ccc(Cn2cc(C(=O)C(=O)O)c3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12fd66ba96c940069272c9107bb28ab0 | Brc1cccc2c1ccn2Cc1ccccc1.OB(O)c1ccc(OC(F)(F)F)cc1>>FC(F)(F)Oc1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1 | C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)Br.ClCCl.C([O-])([O-])=O.[K+].[K+].FC(OC1=CC=C(C=C1)B(O)O)(F)F>>C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F | Br[c:10]1[cH:11][cH:12][cH:13][c:14]2[c:15]1[cH:16][cH:17][n:18]2[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.OB(O)[c:9]1[cH:8][cH:7][c:6]([O:5][C:2]([F:1])([F:3])[F:4])[cH:27][cH:26]1>>[F:1][C:2]([F:3])([F:4])[O:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][c:14]3[c:15]2[cH:16][cH:17][n:18]3[CH2:19][c... | Brc1cccc2c1ccn2Cc1ccccc1.OB(O)c1ccc(OC(F)(F)F)cc1 | FC(F)(F)Oc1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | fbb3b8648e869cd93c2731d6a9721a7097442302f467cc4cb1d3d6bf3de6e845 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3c(-c4ccccc4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[c:9]:[c:10]:2:1.O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C:7]-[#7;a:6]1:[c:8]:[c:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15] | 24.4 | [{"value": 24.0, "product": "C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.4, "product": "C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-benzyl-4-[4-(trifluoromethoxy)phenyl]-1H-indole was prepared by coupling 1-benzyl-4-bromo-1H-indole (0.787 g, 2.75 mmol), and 4-trifluoromethoxyphenylboronic acid (0.683 g, 3.32 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.0679 g, 0.0831 mmol), and po... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cccc2[nH]ccc12.c1ccccc1 | c1ccccc1.c1cccc2[nH]ccc12 | c1ccccc1.c1cccc2[nH]ccc12.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O | null | null | Brc1cccc2c1ccn2Cc1ccccc1.OB(O)c1ccc(OC(F)(F)F)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O>FC(F)(F)Oc1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d41219706994ff0b3f715bb738c1913 | CCO.FC(F)(F)Oc1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(OC(F)(F)F)cc3)c12 | C(C1=CC=CC=C1)N1C=CC2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([O:27][C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[c:34]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11... | CCO.FC(F)(F)Oc1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(OC(F)(F)F)cc3)c12 | null | null | null | C-C Coupling | OtherReaction | 5793860a02afd332539e048290c7a2c0198114fbd04f124edb77c013e70ddad9 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3c(-c4ccccc4)cccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 55 | [{"value": 55.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl {1-benzyl-4-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-4-[4-(trifluoromethoxy)phenyl]-1H-indole (0.243 g, 0.661 mmol), oxalyl chloride (1.03 mL, 13.0 mmol), and ethanol (5 mL) according to the procedure described in Step 3 of Example 1. Purification was carried out by rever... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12 | c1ccccc1.c1cccc2[nH]ccc12.c1ccccc1 | HCl | null | null | null | CCO.FC(F)(F)Oc1ccc(-c2cccc3c2ccn3Cc2ccccc2)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(OC(F)(F)F)cc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4f47ff6a9c5470fa858dcb89456be7d | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(OC(F)(F)F)cc3)c12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(OC(F)(F)F)cc3)c12 | C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]3)[c:32]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(OC(F)(F)F)cc3)c12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(OC(F)(F)F)cc3)c12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3c(-c4ccccc4)cccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 83.5 | [{"value": 83.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.5, "product": "C(C1=CC=CC=C1)N1C=C(C2=C(C=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | {1-Benzyl-4-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-benzyl-4-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate (0.167 g, 0.357 mmol), and potassium hydroxide (0.103 g, 1.84 mmol) in THF (5 mL) and water (5 mL), according to the procedure described in Step 4 of Exampl... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cccc2[nH]ccc12.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(OC(F)(F)F)cc3)c12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cccc(-c3ccc(OC(F)(F)F)cc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d9ca3800bde84f2ebc65ce5c07792f8f | Brc1ccc2ccn(Cc3ccccc3)c2c1.OB(O)c1cccc(Cl)c1>>Clc1cccc(-c2ccc3ccn(Cc4ccccc4)c3c2)c1 | ClC=1C=C(C=CC1)B(O)O.C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)Br.Cl>>C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC(=CC=C1)Cl | Br[c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[cH:22]1.OB(O)[c:6]1[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:23]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][n:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[c:21]3[cH:22]2)[... | Brc1ccc2ccn(Cc3ccccc3)c2c1.OB(O)c1cccc(Cl)c1 | Clc1cccc(-c2ccc3ccn(Cc4ccccc4)c3c2)c1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | e5ead5b904b0190a128418d7442173388e9e1f8d91c97a5f7a23f024c91c663c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]:[c:6]:1):[#7;a:7](-[C:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[#7;a:7](:[c:9]):[c:3]1:[c:4]:[c:5]:[c:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:2]:1 | 50 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | 3-Chlorophenylboronic acid (1.21 g, 7.76 mmol) was added in four poritions to the mixture of 1-benzyl-6-bromo-1H-indole (1.12 g, 3.91 mmol), palladium(II) acetate (0.0191 g, 0,0850 mmol), and tetrabutylammonium bromide (1.26 g, 3.91 mmol) in water (22.5 mL) and THF (2.5 mL) while heating at 70° C. for 4 hours. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccccc1.c1ccc2cc[nH]c2c1 | c1ccccc1.c1ccc2cc[nH]c2c1.c1ccccc1 | HBr.B | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C1CCOC1 | 70 | null | Brc1ccc2ccn(Cc3ccccc3)c2c1.OB(O)c1cccc(Cl)c1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C1CCOC1>Clc1cccc(-c2ccc3ccn(Cc4ccccc4)c3c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-54c6797d71ce469d8c720a7128800180 | CCO.Clc1cccc(-c2ccc3ccn(Cc4ccccc4)c3c2)c1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3cccc(Cl)c3)ccc12 | C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC(=CC=C1)Cl.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC(=CC=C1)Cl)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]3)[cH:28][cH:29][c:30]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:1... | CCO.Clc1cccc(-c2ccc3ccn(Cc4ccccc4)c3c2)c1.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3cccc(Cl)c3)ccc12 | null | null | null | C-C Coupling | OtherReaction | 34ba1cef5b600f2468b9a4fe43ff5669afe09e6688a408ea8eae10e83b03a2fa | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 67 | [{"value": 67.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl [1-benzyl-6-(3-chlorophenyl)-1H-indol-3-yl](oxo)acetate was prepared from 1-benzyl-6-(3-chlorophenyl)-1H-indole (0.591 g, 1.86 mmol), oxalyl chloride (0.49 mL, 5.6 mmol), and ethanol (2 mL) following the procedure described in Step 3 of Example 1. Purification by flash chromatography using 5-100% ethyl acetate in... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccccc1.c1ccc2cc[nH]c2c1.c1ccccc1 | HCl | null | null | null | CCO.Clc1cccc(-c2ccc3ccn(Cc4ccccc4)c3c2)c1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3cccc(Cl)c3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff7eb60b2bd344bc8338bd32206e0039 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3cccc(Cl)c3)ccc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3cccc(Cl)c3)ccc12 | C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC(=CC=C1)Cl)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC(=CC=C1)Cl)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]([Cl:24])[cH:25]3)[cH:26][cH:27][c:28]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3cccc(Cl)c3)ccc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3cccc(Cl)c3)ccc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 60.3 | [{"value": 60.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC(=CC=C1)Cl)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.3, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC(=CC=C1)Cl)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | {1-Benzyl-6-(3-chlorophenyl)-1H-indol-3-yl](oxo)acetic acid was prepared from ethyl [1-benzyl-6-(3-chlorophenyl)-1H-indol-3-yl](oxo)acetate (0.489 g, 1.17 mmol), and potassium hydroxide (0.214 g, 3.81 mmol) in THF (10 mL) and water (10 mL), according to the procedure described in Step 4 of Example 5. Crystallization fr... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2cc[nH]c2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3cccc(Cl)c3)ccc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3cccc(Cl)c3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1fe7703d3aa2480d97d9b92cefa78595 | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1cccc(OC(F)(F)F)c1>>FC(F)(F)Oc1cccc(-c2ccc3c(ccn3Cc3ccccc3)c2)c1 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br.C([O-])([O-])=O.[K+].[K+].FC(OC=1C=C(C=CC1)B(O)O)(F)F>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F | Br[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16][cH:17][n:18]2[CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26]1.OB(O)[c:10]1[cH:9][cH:8][cH:7][c:6]([O:5][C:2]([F:1])([F:3])[F:4])[cH:27]1>>[F:1][C:2]([F:3])([F:4])[O:5][c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16][cH:17][n:18]3[CH2:19]... | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1cccc(OC(F)(F)F)c1 | FC(F)(F)Oc1cccc(-c2ccc3c(ccn3Cc3ccccc3)c2)c1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 38 | [{"value": 38.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.6, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (2.28 g, 7.97 mmol), and 3-(trifluoromethoxy)phenylboronic acid (1.66 g, 8.06 mmol), using potassium carbonate (2.75, 19.9 mmol), palladium(II) acetate (0.0731 g, 0.326 mmol), and tetrabutylammonium bromide (2.78 g, 8.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C1CCOC1 | null | null | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1cccc(OC(F)(F)F)c1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C1CCOC1>FC(F)(F)Oc1cccc(-c2ccc3c(ccn3Cc3ccccc3)c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-badc7a3f16094e92b02f5d5e439fc492 | CCO.FC(F)(F)Oc1cccc(-c2ccc3c(ccn3Cc3ccccc3)c2)c1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cccc(OC(F)(F)F)c3)cc12 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][c:26]([O:27][C:28]([F:29])([F:30])[F:31])[cH:32]3)[cH:33][c:34]12.Cl[C:4](=[O:5])[C:6](Cl)=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11... | CCO.FC(F)(F)Oc1cccc(-c2ccc3c(ccn3Cc3ccccc3)c2)c1.O=C(Cl)C(=O)Cl | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cccc(OC(F)(F)F)c3)cc12 | null | null | null | C-C Coupling | OtherReaction | e42beb79999369525e781f5f2a8c25a764f237d2f2302bca9902d8152413d7f2 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 84 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl {1-benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indole (1.06 g, 2.89 mmol), oxalyl chloride (1.04 mL, 13.0 mmol), and ethanol (1.5 mL), following the procedure described in Step 3 of Example 1. Purification by flash chromatography us... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | null | null | null | CCO.FC(F)(F)Oc1cccc(-c2ccc3c(ccn3Cc3ccccc3)c2)c1.O=C(Cl)C(=O)Cl>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cccc(OC(F)(F)F)c3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0806f19de3fb4a4a97a0f00c5942ad35 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cccc(OC(F)(F)F)c3)cc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cccc(OC(F)(F)F)c3)cc12 | C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30]3)[cH:31][c:32]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cccc(OC(F)(F)F)c3)cc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cccc(OC(F)(F)F)c3)cc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 56.5 | [{"value": 54.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.5, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=CC=C1)OC(F)(F)F)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate (1.1 g, 2.4 mmol), and potassium hydroxide (0.44 g, 7.8 mmol) in THF (25 mL) and water (25 mL), according to the procedure described in Step 4 of Example 5. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cccc(OC(F)(F)F)c3)cc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3cccc(OC(F)(F)F)c3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-43c553875590465da8a05c27dc2ef3b3 | Brc1ccc2ccn(Cc3ccccc3)c2c1.OB(O)c1ccccc1>>c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)Br.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C.C1(=CC=CC=C1)B(O)O>>C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=CC=C1 | Br[c:12]1[cH:11][cH:10][c:9]2[cH:8][cH:7][n:6]([CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:22][cH:21]3)[c:20]2[cH:19]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][n:6]2[cH:7][cH:8][c:9]3[cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19][c:20]23)[cH:21][cH:22]1 | Brc1ccc2ccn(Cc3ccccc3)c2c1.OB(O)c1ccccc1 | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | 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.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | e5ead5b904b0190a128418d7442173388e9e1f8d91c97a5f7a23f024c91c663c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5](:[c:6]:1):[#7;a:7](-[C:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[c:6]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:2]:[c:3]:[c:4]:1 | 58.4 | [{"value": 58.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.4, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-6-phenyl-1H-indole was prepared by coupling 1-benzyl-6-bromo-1H-indole (3.48 g , 12.2 mmol), and phenylboronic acid (1.63 g, 13.4 mmol), using tetrakis(triphenylphosphine)palladium (0.976 g, 0.846 mmol), and sodium carbonate (5.2 g, 49 mmol) in water (25 mL), ethanol (5 mL), and toluene (55 mL), according to t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccc2cc[nH]c2c1.c1ccccc1 | c1ccccc1.c1ccc2cc[nH]c2c1.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.O.C(C)O | null | null | Brc1ccc2ccn(Cc3ccccc3)c2c1.OB(O)c1ccccc1>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.C(C)O>c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-353b87ec96154b5fafe552d804dc1405 | CCO.O=C(Cl)C(=O)Cl.c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccccc3)ccc12 | C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=CC=C1.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=CC=C1)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].Cl[C:4](=[O:5])[C:6](Cl)=[O:7].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[cH:27][cH:28][c:29]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16... | CCO.O=C(Cl)C(=O)Cl.c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccccc3)ccc12 | null | null | null | C-C Coupling | OtherReaction | 34ba1cef5b600f2468b9a4fe43ff5669afe09e6688a408ea8eae10e83b03a2fa | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 77 | [{"value": 77.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=CC=C1)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl (1-benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetate was prepared from, 1-benzyl-6-phenyl-1H-indole (1.90 g, 6.71 mmol), oxalyl chloride (1.8 mL, 20 mmol), and ethanol (4 mL). Purification by flash chromatography, using 5-12.5% ethyl acetate in hexane as an eluant, yielded the title compound as a light yellow solid (1.9... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccccc1.c1ccc2cc[nH]c2c1.c1ccccc1 | HCl | null | null | null | CCO.O=C(Cl)C(=O)Cl.c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccccc3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b1b435b5c7164b11969b175b4669fac3 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccccc3)ccc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccccc3)ccc12 | C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=CC=C1)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=CC=C1)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][cH:26][c:27]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18](-[c:19... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccccc3)ccc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccccc3)ccc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3ccc(-c4ccccc4)cc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 70 | [{"value": 70.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=CC=C1)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=C(C=C12)C1=CC=CC=C1)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (1-Benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetic acid was prepared from ethyl (1-benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetate (1.90 g, 4.96 mmol), and potassium hydroxide (0.856 g, 15.3 mmol) in THF (20 mL) and water (20 mL), following the procedure described in Step 4 of Example 5. Crystallization from acetonitrile and dryi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2cc[nH]c2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccccc3)ccc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2cc(-c3ccccc3)ccc12 |
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