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-0387783899c642a8b7eb4ba379bcdf5d | ord-cf6e582b3420469ba395e08f1c797454 | Brc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc2nonc12.CNCCOC>>COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc2nonc12 | COCCNC.O.BrC1=NN=C(N1C1=CC=CC2=NON=C21)C=2C=NC(=CC2)C2=CC=CC=C2>>N=1ON=C2C1C=CC=C2N2C(=NN=C2C=2C=NC(=CC2)C2=CC=CC=C2)N(C)CCOC | Br[c:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21][cH:22]2)[n:23]1-[c:24]1[cH:25][cH:26][cH:27][c:28]2[n:29][o:30][n:31][c:32]12.[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6]>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[c:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][cH:13][c:14](-[c... | Brc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc2nonc12.CNCCOC | COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc2nonc12 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1c5140a16b98c8622dd561f15d9064ef2d9e3793a6123294dacf3a1a1e648482 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(-c2ccc(-c3nncn3-c3cccc4nonc34)cn2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4](-[c:5]:[c:6]:[#7;a:7]):[#7;a:8]:1-[c:9]:[c:10]:[#7;a:11].[C:12]-[C:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[#7;a:7]:[c:6]:[c:5]-[c:4]1:[#7;a:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:15])-[C:13]-[C:12]):[#7;a:8]:1-[c:9]:[c:10]:[#7;a:11] | 19 | [{"value": 19.0, "product": "N=1ON=C2C1C=CC=C2N2C(=NN=C2C=2C=NC(=CC2)C2=CC=CC=C2)N(C)CCOC", "details": "PERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | 6 | HOUR | In a sealed tube, N-(2-methoxyethyl)methylamine (3 ml) and water (3 ml) were added to 4-[3-bromo-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2,1,3-benzooxadiazol (336 mg) prepared in the Production Example 5, and stirred at 160° C. for 6 hours. After the reaction solution was cooled to ambient temperature, chlorofo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1nc[nH]n1 | c1nc[nH]n1 | c1nc[nH]n1.c1ccncc1.c1ccccc1.c1ccc2nonc2c1 | HBr | C(Cl)(Cl)Cl | 160 | 6 | Brc1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc2nonc12.CNCCOC>C(Cl)(Cl)Cl>COCCN(C)c1nnc(-c2ccc(-c3ccccc3)nc2)n1-c1cccc2nonc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-815da08f3f394f2f9fe1d635be980f9a | O=C(NNC(=S)Nc1ccccc1F)c1ccc(-c2ccccc2)cc1>>Fc1ccccc1-n1c(S)nnc1-c1ccc(-c2ccccc2)cc1 | C1(=CC=C(C=C1)C(=O)NNC(=S)NC1=C(C=CC=C1)F)C1=CC=CC=C1.Cl>>C1(=CC=C(C=C1)C=1N(C(=NN1)S)C1=C(C=CC=C1)F)C1=CC=CC=C1 | O=[C:13]([NH:12][NH:11][C:9]([NH:8][c:7]1[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]1)=[S:10])[c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[n:8]1[c:9]([SH:10])[n:11][n:12][c:13]1-[c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:... | O=C(NNC(=S)Nc1ccccc1F)c1ccc(-c2ccccc2)cc1 | Fc1ccccc1-n1c(S)nnc1-c1ccc(-c2ccccc2)cc1 | null | null | [OH-].[Na+] | Aromatic Heterocycle Formation | OtherReaction | 1144bd2dd2884a2ad222a26ff69bf4b180d1a69c57c6d5800b04ac08cd859d55 | bd25a921a2c629db55acdd4e6573a984608495ab82bd2f024888ad689a9b3a51 | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cc2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[S;H0;D1;+0:5])-[NH;D2;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[F;D1;H0:11]-[c:10](:[c:12]):[c;H0;D3;+0:7](-[n;H0;D3;+0:6]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]):[... | 97.4 | [{"value": 97.0, "product": "C1(=CC=C(C=C1)C=1N(C(=NN1)S)C1=C(C=CC=C1)F)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "C1(=CC=C(C=C1)C=1N(C(=NN1)S)C1=C(C=CC=C1)F)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(Biphenyl-4-carbonyl)-4-(2-fluorophenyl)thiosemicarbazide (12.1 g) was suspended in aqueous 2 mol/liter sodium hydroxide solution (300 ml), and refluxed under heating for 3 hours. After the reaction solution was cooled to ambient temperature, the solution was neutralized under ice cooling with conc. hydrochloric acid... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Thiourea | Aromatic thiol | null | c1nnc[nH]1 | c1ccccc1.c1nnc[nH]1.c1ccccc1.c1ccccc1 | HO- | [OH-].[Na+] | null | null | O=C(NNC(=S)Nc1ccccc1F)c1ccc(-c2ccccc2)cc1>[OH-].[Na+]>Fc1ccccc1-n1c(S)nnc1-c1ccc(-c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba454e8e73744cc58e8043ddd323cb9f | CI.Fc1ccccc1-n1c(S)nnc1-c1ccc(-c2ccccc2)cc1>>CSc1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F | O.CI.C([O-])([O-])=O.[K+].[K+].C1(=CC=C(C=C1)C=1N(C(=NN1)S)C1=C(C=CC=C1)F)C1=CC=CC=C1>>C1(=CC=C(C=C1)C1=NN=C(N1C1=C(C=CC=C1)F)SC)C1=CC=CC=C1 | I[CH3:1].[SH:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[n:19]1-[c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[F:26]>>[CH3:1][S:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[n:19]1-[c:20]1[c... | CI.Fc1ccccc1-n1c(S)nnc1-c1ccc(-c2ccccc2)cc1 | CSc1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | thioether_nucl_sub | cbeef1e4b9250d05ec80fbfc2f139c184e610b2c8de8aec4214044a1d69bd441 | a20e50d7df818b91ffc2e826d304ad74f6246978a284c599e867e2d806b7437e | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cc2)cc1 | I-[CH3;D1;+0:1].[SH;D1;+0:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8]>>[CH3;D1;+0:1]-[S;H0;D2;+0:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8] | 72.5 | [{"value": 72.0, "product": "C1(=CC=C(C=C1)C1=NN=C(N1C1=C(C=CC=C1)F)SC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.5, "product": "C1(=CC=C(C=C1)C1=NN=C(N1C1=C(C=CC=C1)F)SC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 5-Biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazole-3-thiol (2.7 g) was dissolved in acetonitrile (50 ml), followed by addition of methyl iodide (0.967 ml) and potassium carbonate (1.07 g), and stirred at ambient temperature for 3 hours. Water was added to the reaction solution, followed by extraction with chloroform.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Monosulfide | null | null | c1nc[nH]n1.c1ccccc1.c1ccccc1.c1ccccc1 | HI | C(C)#N | null | 3 | CI.Fc1ccccc1-n1c(S)nnc1-c1ccc(-c2ccccc2)cc1>C(C)#N>CSc1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-292a0a704b9b471094fb6636feb1e86e | Nc1ccccc1F.O=C(COCc1ccccc1)NNC(=O)c1ccc(-c2ccccc2)cc1>>Fc1ccccc1-n1c(COCc2ccccc2)nnc1-c1ccc(-c2ccccc2)cc1 | C(C1=CC=CC=C1)OCC(=O)NNC(=O)C1=CC=C(C=C1)C1=CC=CC=C1.P(=O)(Cl)(Cl)Cl.FC1=C(N)C=CC=C1>>C(C1=CC=CC=C1)OCC1=NN=C(N1C1=C(C=CC=C1)F)C1=CC=C(C=C1)C1=CC=CC=C1 | [F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH2:8].O=[C:9]([CH2:10][O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[NH:19][NH:20][C:21](=O)[c:22]1[cH:23][cH:24][c:25](-[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:32][cH:33]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[n:8]1[c:9]([CH2:10][O:11][CH2:12][c:13]2... | Nc1ccccc1F.O=C(COCc1ccccc1)NNC(=O)c1ccc(-c2ccccc2)cc1 | Fc1ccccc1-n1c(COCc2ccccc2)nnc1-c1ccc(-c2ccccc2)cc1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 1491874fb5fa5a2454282fe5563ef779325446dc805436f30dc5afd38438560d | 1f5c57f9ffab8a5214b697412c1715772187bdfe92c542c30f8b933239b9a67f | c1ccc(COCc2nnc(-c3ccc(-c4ccccc4)cc3)n2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5]-[#8:6])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[F;D1;H0:12]-[c:13](:[c:14]):[c;H0;D3;+0:15](-[NH2;D1;+0:16]):[c:17]:[c:18]>>[#8:6]-[C:5]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:3]:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H... | 58 | [{"value": 58.0, "product": "C(C1=CC=CC=C1)OCC1=NN=C(N1C1=C(C=CC=C1)F)C1=CC=C(C=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | HOUR | To biphenyl-4-carboxylic acid N′-(2-benzyloxyacetyl)hydrazide (9.38 g) was added phosphorus oxychloride (30 ml), and stirred at 100° C. for one hour. After the reaction solution was cooled to ambient temperature, the reaction solution was concentrated under reduced pressure. To the resulting residue was added ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Primary amine | null | null | c1nnc[nH]1 | c1ccccc1.c1ccccc1.c1nnc[nH]1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)OCC | 100 | 1 | Nc1ccccc1F.O=C(COCc1ccccc1)NNC(=O)c1ccc(-c2ccccc2)cc1>C(C)(=O)OCC>Fc1ccccc1-n1c(COCc2ccccc2)nnc1-c1ccc(-c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72a613d6a0154eb18a05f5ad89f90f0a | Fc1ccccc1-n1c(COCc2ccccc2)nnc1-c1ccc(-c2ccccc2)cc1>>OCc1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F | B(Cl)(Cl)Cl.CCCCCC.C(C1=CC=CC=C1)OCC1=NN=C(N1C1=C(C=CC=C1)F)C1=CC=C(C=C1)C1=CC=CC=C1.CO.C(O)([O-])=O.[Na+]>>C1(=CC=C(C=C1)C=1N(C(=NN1)CO)C1=C(C=CC=C1)F)C1=CC=CC=C1 | c1ccc(C[O:1][CH2:2][c:3]2[n:4][n:5][c:6](-[c:7]3[cH:8][cH:9][c:10](-[c:11]4[cH:12][cH:13][cH:14][cH:15][cH:16]4)[cH:17][cH:18]3)[n:19]2-[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[F:26])cc1>>[OH:1][CH2:2][c:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[n:19]1-... | Fc1ccccc1-n1c(COCc2ccccc2)nnc1-c1ccc(-c2ccccc2)cc1 | OCc1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F | null | null | C(Cl)(Cl)Cl | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cc2)cc1 | [#7;a:1]:[c:2](-[C:3]-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1):[#7;a:5]:[#7;a:6]>>[#7;a:1]:[c:2](-[C:3]-[OH;D1;+0:4]):[#7;a:5]:[#7;a:6] | 44 | [{"value": 44.0, "product": "C1(=CC=C(C=C1)C=1N(C(=NN1)CO)C1=C(C=CC=C1)F)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.9, "product": "C1(=CC=C(C=C1)C=1N(C(=NN1)CO)C1=C(C=CC=C1)F)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 3-Benzyloxymethyl-5-biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazole (6.00 g) was dissolved in chloroform (200 ml), followed by dropwise addition of 1 mol/liter boron trichloride-hexane solution (30 ml) at −44° C. and stirred at the same temperature for 30 minutes and at ambient temperature for one hour. To the react... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | c1nc[nH]n1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(Cl)(Cl)Cl | null | 1 | Fc1ccccc1-n1c(COCc2ccccc2)nnc1-c1ccc(-c2ccccc2)cc1>C(Cl)(Cl)Cl>OCc1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6dc921bf4d444f74b81d08626569b52f | O=S(Cl)Cl.OCc1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F>>Fc1ccccc1-n1c(CCl)nnc1-c1ccc(-c2ccccc2)cc1 | C1(=CC=C(C=C1)C=1N(C(=NN1)CO)C1=C(C=CC=C1)F)C1=CC=CC=C1.S(=O)(Cl)Cl.C(Cl)(Cl)Cl>>C1(=CC=C(C=C1)C1=NN=C(N1C1=C(C=CC=C1)F)CCl)C1=CC=CC=C1 | O=S(Cl)[Cl:11].O[CH2:10][c:9]1[n:8](-[c:7]2[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]2)[c:14](-[c:15]2[cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][cH:26]2)[n:13][n:12]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[n:8]1[c:9]([CH2:10][Cl:11])[n:12][n:13][c:14]1-[c:15]1[cH:16][cH:17][c:18](-[c:19]2[... | O=S(Cl)Cl.OCc1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F | Fc1ccccc1-n1c(CCl)nnc1-c1ccc(-c2ccccc2)cc1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc(-c2ccc(-c3nncn3-c3ccccc3)cc2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8] | 81 | [{"value": 81.0, "product": "C1(=CC=C(C=C1)C1=NN=C(N1C1=C(C=CC=C1)F)CCl)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 5 | HOUR | [5-Biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]methanol (1.81 g) was suspended in toluene (25 ml), followed by addition of thionyl chloride (1.5 ml) and chloroform (25 ml), and stirred at 60° C. for 5 hours. After the reaction solution was concentrated under reduced pressure, ethyl acetate was added to the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.c1nnc[nH]1.c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | 60 | 5 | O=S(Cl)Cl.OCc1nnc(-c2ccc(-c3ccccc3)cc2)n1-c1ccccc1F>C1(=CC=CC=C1)C>Fc1ccccc1-n1c(CCl)nnc1-c1ccc(-c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7794f3c01c4a42198c2584e503f849f8 | C1COCCN1.Fc1ccccc1-n1c(CCl)nnc1-c1ccc(-c2ccccc2)cc1>>Fc1ccccc1-n1c(CN2CCOCC2)nnc1-c1ccc(-c2ccccc2)cc1 | N1CCOCC1.[H-].[Na+].C1(=CC=C(C=C1)C1=NN=C(N1C1=C(C=CC=C1)F)CCl)C1=CC=CC=C1>>C1(=CC=C(C=C1)C=1N(C(=NN1)CN1CCOCC1)C1=C(C=CC=C1)F)C1=CC=CC=C1 | [NH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.Cl[CH2:10][c:9]1[n:8](-[c:7]2[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]2)[c:19](-[c:20]2[cH:21][cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][cH:31]2)[n:18][n:17]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[n:8]1[c:9]([CH2:10][N:11]2[CH2:12][CH2:13][O:14][C... | C1COCCN1.Fc1ccccc1-n1c(CCl)nnc1-c1ccc(-c2ccccc2)cc1 | Fc1ccccc1-n1c(CN2CCOCC2)nnc1-c1ccc(-c2ccccc2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2ccc(-c3nnc(CN4CCOCC4)n3-c3ccccc3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[c:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[c:7]-[#7;a:6]1:[c:5]:[#7;a:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1 | 74 | [{"value": 74.0, "product": "C1(=CC=C(C=C1)C=1N(C(=NN1)CN1CCOCC1)C1=C(C=CC=C1)F)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Morpholine (0.599 ml) was dissolved in N,N-dimethylformamide (6 ml), followed by addition of sodium hydride (60%, 275 mg) under ice cooling, and stirred at the same temperature for 30 minutes. Under ice cooling, 3-biphenyl-4-yl-5-chloromethyl-4-(2-fluorophenyl)-4H-1,2,4-triazole (599 mg) was added to the reaction solut... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.c1nnc[nH]1.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | 0.5 | C1COCCN1.Fc1ccccc1-n1c(CCl)nnc1-c1ccc(-c2ccccc2)cc1>CN(C=O)C>Fc1ccccc1-n1c(CN2CCOCC2)nnc1-c1ccc(-c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eede2b3d64ad403cbc6219dd7b894bcc | COC1CCCO1.c1cnc2[nH]ccc2c1>>OCCCC(c1c[nH]c2ncccc12)c1c[nH]c2ncccc12 | N1C=CC2=CC=CN=C12.COC1OCCC1>>N1C=C(C2=CC=CN=C12)C(CCCO)C1=CNC2=NC=CC=C12 | O([CH:5]1[O:1][CH2:2][CH2:3][CH2:4]1)[CH3:11].[cH:6]1[cH:7][nH:8][c:9]2[c:14]1[cH:13][cH:12][cH:20][n:19]2>>[OH:1][CH2:2][CH2:3][CH2:4][CH:5]([c:6]1[cH:7][nH:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]12)[c:15]1[cH:16][nH:17][c:18]2[n:19][cH:20][cH:21][cH:22][c:23]12 | COC1CCCO1.c1cnc2[nH]ccc2c1 | OCCCC(c1c[nH]c2ncccc12)c1c[nH]c2ncccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 60739617603a0725721d97ef4dccb686c3e557f71265e15aa108cdeb9d4a01ff | f4039f6137c58f023c0dcbef20c5fb1b1eb5a4818bb4583d7316df6dacf02876 | c1cnc2[nH]cc(Cc3c[nH]c4ncccc34)c2c1 | [#7;a:1]1:[c:2]:[cH;D2;+0:3]:[c:4]2:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[n;H0;D2;+0:8]:[c;H0;D3;+0:9]:1:2.[CH3;D1;+0:10]-O-[CH;D3;+0:11]1-[C:12]-[C:13]-[C:14]-[O;H0;D2;+0:15]-1>>[OH;D1;+0:15]-[C:14]-[C:13]-[C:12]-[CH;D3;+0:11](-[c:16]1:[c:17]:[#7;a:18]:[c:19]2:[n;H0;D2;+0:8]:[cH;D2;+0:7]:[c:20]:[c:21]:[c:22]:1:2)-[c;H0;D3;... | null | [] | null | null | null | null | This compound is prepared in the same way as described in example 1/1 starting from 7-azaindol and 2-methoxy-tetrahydrofuran.
Conditions: See reaction.notes.procedure_details.
Workup: This compound is prepared in the same way | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOC1.c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1.c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1.c1cnc2[nH]ccc2c1 | null | null | null | null | COC1CCCO1.c1cnc2[nH]ccc2c1>>OCCCC(c1c[nH]c2ncccc12)c1c[nH]c2ncccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7069c89951542c6aac014e0ba0b4104 | CCCC=O.c1ccc2[nH]ccc2c1>>CCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12 | N1C=CC2=CC=CC=C12.C(CCC)=O>>N1C=C(C2=CC=CC=C12)C(CCC)C1=CNC2=CC=CC=C12 | O=[CH:4][CH2:3][CH2:2][CH3:1].[cH:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12)[c:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | CCCC=O.c1ccc2[nH]ccc2c1 | CCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12 | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | 7478ef73472b362e627cc75f333e4944966fb671972736fb7b88535ca746eb04 | 208b563f3abf251ea7444c9cd3c4f06a2ed6563578ed1cbc46d48e2aa059bd9b | c1ccc2c(Cc3c[nH]c4ccccc34)c[nH]c2c1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5]1:[cH;D2;+0:6]:[c:7]:[#7;a:8]:[c:9]:1:[c:10]>>[C:3]-[C:2]-[CH;D3;+0:1](-[c:11](:[c:12]):[c:13])-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9](:[c:10]):[c:5]:1:[c:4] | null | [] | null | null | null | null | 282 mg of indole (2.4 mmol) were dissolved in 10 ml of CH3OH and 5 ml of H2O; 72 mg (1 mmol) of butyraldehyde and 240 mg of dysprosium triflate-(CF3SO3)3Dy-(0.393 mmol) were added.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | null | CO.O | null | null | CCCC=O.c1ccc2[nH]ccc2c1>CO.O>CCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f5f5a80157ad4bdca616f4b651e2eecb | CCCC=O.O=[N+]([O-])c1ccc2[nH]ccc2c1>>CCCC(c1c[nH]c2ccc([N+](=O)[O-])cc12)c1c[nH]c2ccc([N+](=O)[O-])cc12 | [N+](=O)([O-])C=1C=C2C=CNC2=CC1.C(CCC)=O>>[N+](=O)([O-])C=1C=C2C(=CNC2=CC1)C(CCC)C1=CNC2=CC=C(C=C12)[N+](=O)[O-] | [CH3:1][CH2:2][CH2:3][CH:4]=[O:13].[cH:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][c:23]([N+:24]([O-:14])=[O:25])[cH:27][c:16]12>>[CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]12)[c:17]1[cH:18][nH:19][c:20]2[cH:21][cH:22][c:23]([N+:24](=[O:25])[O-:26])[cH:27][c:28]1... | CCCC=O.O=[N+]([O-])c1ccc2[nH]ccc2c1 | CCCC(c1c[nH]c2ccc([N+](=O)[O-])cc12)c1c[nH]c2ccc([N+](=O)[O-])cc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 02371de143030bb6675629fd0d2b1da4e29d09cf183a8777e6aa524bfe2352b9 | c192aaf31db94f00670e2c5a2d22e644d14ddc3b1ea4f4f1f58ffb114905b5a5 | c1ccc2c(Cc3c[nH]c4ccccc34)c[nH]c2c1 | [C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4].[O-;H0;D1:5]-[N+;H0;D3:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[c:10]:[c:11]2:[#7;a:12]:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15]:2:[cH;D2;+0:16]:1>>[C:1]-[C:2]-[CH;D3;+0:3](-[c:17](:[c:18]):[c:19]1:[c:20]:[c:21]:[c:22]:[c;H0;D3;+0:8](-[N+;H0;D3:6](-[O;-;D1;H0:23])=[O;D1;H0:7]):... | null | [] | null | null | null | null | ST 1429 was prepared from 5-nitroindole and butyraldehyde prepared using the method described in example 2/1.
Conditions: See reaction.notes.procedure_details.
Workup: prepared | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Nitro group.Nitro group | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CCCC=O.O=[N+]([O-])c1ccc2[nH]ccc2c1>>CCCC(c1c[nH]c2ccc([N+](=O)[O-])cc12)c1c[nH]c2ccc([N+](=O)[O-])cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40492c21a69f46b88fd0fa2d519864ca | CCCC=O.Fc1ccc2[nH]ccc2c1>>CCCC(c1c[nH]c2ccc(F)cc12)c1c[nH]c2ccc(F)cc12 | FC=1C=C2C=CNC2=CC1.C(CCC)=O>>FC=1C=C2C(=CNC2=CC1)C(CCC)C1=CNC2=CC=C(C=C12)F | O=[CH:4][CH2:3][CH2:2][CH3:1].[cH:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]12>>[CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]12)[c:15]1[cH:16][nH:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][c:24]12 | CCCC=O.Fc1ccc2[nH]ccc2c1 | CCCC(c1c[nH]c2ccc(F)cc12)c1c[nH]c2ccc(F)cc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ec460e45d4b7f4f683438c9409b11235f5dae08ccdc80957cd49fe1fd35b87d0 | 31aeef82055455d7a38ad7be94e5da21cccc4998cb40f7eea686b19a2150757f | c1ccc2c(Cc3c[nH]c4ccccc34)c[nH]c2c1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5]1:[cH;D2;+0:6]:[c:7]:[#7;a:8]:[c:9]:1:[c:10]>>[C:3]-[C:2]-[CH;D3;+0:1](-[c:11](:[c:12]):[c:13])-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9](:[c:10]):[c:5]:1:[c:4] | 45 | [{"value": 45.0, "product": "FC=1C=C2C(=CNC2=CC1)C(CCC)C1=CNC2=CC=C(C=C12)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared in the same way as described in example 2/2 starting from 5-fluoroindole and butyraldehyde. The reaction, however, was heated under reflux for 24 hours. The end product was isolated and purified by chromatography on an SiO2 column using a hexane:ethyl ether gradient ranging from 7:3 to 4:6 as the elue... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Aromatic halide | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | null | null | null | null | CCCC=O.Fc1ccc2[nH]ccc2c1>>CCCC(c1c[nH]c2ccc(F)cc12)c1c[nH]c2ccc(F)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e699b14c36a4cb1ab9bfad78d80f704 | CCCC=O.c1cnc2[nH]ccc2c1>>CCCC(c1c[nH]c2ncccc12)c1c[nH]c2ncccc12 | N1C=CC2=CC=CN=C12.C(CCC)=O>>N1C=C(C2=CC=CN=C12)C(CCC)C1=CNC2=NC=CC=C12 | O=[CH:4][CH2:3][CH2:2][CH3:1].[cH:5]1[cH:6][nH:7][c:8]2[c:13]1[cH:12][cH:11][cH:19][n:18]2>>[CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][nH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]12)[c:14]1[cH:15][nH:16][c:17]2[n:18][cH:19][cH:20][cH:21][c:22]12 | CCCC=O.c1cnc2[nH]ccc2c1 | CCCC(c1c[nH]c2ncccc12)c1c[nH]c2ncccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 808e4420e445f28e4eb1512fcdbecfad15d93171379a5ec564a53c5e21e27a6b | 208b563f3abf251ea7444c9cd3c4f06a2ed6563578ed1cbc46d48e2aa059bd9b | c1cnc2[nH]cc(Cc3c[nH]c4ncccc34)c2c1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[#7;a:4]1:[c:5]:[cH;D2;+0:6]:[c:7]2:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:1:2>>[C:3]-[C:2]-[CH;D3;+0:1](-[c:13]1:[c:14]:[#7;a:15]:[c:16]2:[n;H0;D2;+0:11]:[cH;D2;+0:10]:[c:17]:[c:18]:[c:19]:1:2)-[c;H0;D3;+0:6]1:[c:5]:[#7;a:4]:[c;H0;D3;+0:12]2:[#7;a:20]:[c:21]:[cH;D2;... | 15 | [{"value": 15.0, "product": "N1C=C(C2=CC=CN=C12)C(CCC)C1=CNC2=NC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | ST 1436 was prepared as described in example 2/2 from 7-azaindole and butyraldehyde. The reaction, however, was heated under reflux for 48 hours. The end product was isolated and purified chromatographically on a silica column eluting with a CH2Cl2:CH3COCH3 gradient ranging from 9:1 to 4:6. Yield 15%.
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1.c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1.c1cnc2[nH]ccc2c1 | null | null | null | null | CCCC=O.c1cnc2[nH]ccc2c1>>CCCC(c1c[nH]c2ncccc12)c1c[nH]c2ncccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04e0ea007ddc44a8939ea2cef695c555 | CCCCCCCCCCCCCC=O.c1ccc2[nH]ccc2c1>>CCCCCCCCCCCCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12 | N1C=CC2=CC=CC=C12.C(CCCCCCCCCCCCC)=O>>N1C=C(C2=CC=CC=C12)C(CCCCCCCCCCCCC)C1=CNC2=CC=CC=C12 | O=[CH:25][CH2:24][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH3:1].[cH:15]1[cH:16][nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([c:15]1[cH:16][nH:17][c:18]2[cH:19][cH:20][... | CCCCCCCCCCCCCC=O.c1ccc2[nH]ccc2c1 | CCCCCCCCCCCCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 7478ef73472b362e627cc75f333e4944966fb671972736fb7b88535ca746eb04 | 208b563f3abf251ea7444c9cd3c4f06a2ed6563578ed1cbc46d48e2aa059bd9b | c1ccc2c(Cc3c[nH]c4ccccc34)c[nH]c2c1 | O=[CH;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C:4]-[C:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[CH3;D1;+0:9].[c:10]:[c:11]1:[#7;a:12]:[c:13]:[cH;D2;+0:14]:[c:15]:1:[c:16]>>[C:6]-[C:7]-[CH2;D2;+0:8]-[C:17]-[C:18]-[CH3;D1;+0:9].[C:5]-[C:4]-[CH;D3;+0:3](-[c;H0;D3;+0:14]1:[c:13]:[#7;a:12]:[c:11](:[c:10]):[c:15]:1:[c:16])-[c;H0;D3;+0:2]1... | 80 | [{"value": 80.0, "product": "N1C=C(C2=CC=CC=C12)C(CCCCCCCCCCCCC)C1=CNC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound was prepared as described in example 2/4, reacting the indole with tetradecane aldehyde. Yield 80%.
Conditions: See reaction.notes.procedure_details.
Workup: The compound was prepared | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | null | null | null | null | CCCCCCCCCCCCCC=O.c1ccc2[nH]ccc2c1>>CCCCCCCCCCCCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34ed5aa2890246b9ad2d8473b2804b63 | CCCC=O.c1cc[nH]c1>>CCCC(c1ccc[nH]1)c1ccc[nH]1 | N1C=CC=C1.C(CCC)=O>>N1C(=CC=C1)C(CCC)C=1NC=CC1 | O=[CH:4][CH2:3][CH2:2][CH3:1].[cH:5]1[cH:6][cH:7][cH:8][nH:9]1>>[CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][cH:7][cH:8][nH:9]1)[c:10]1[cH:11][cH:12][cH:13][nH:14]1 | CCCC=O.c1cc[nH]c1 | CCCC(c1ccc[nH]1)c1ccc[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b732ccc2ebe5ae50bce53fc187224a141e12227e8b603f4b5e25f82a4de1cafe | 208b563f3abf251ea7444c9cd3c4f06a2ed6563578ed1cbc46d48e2aa059bd9b | c1c[nH]c(Cc2ccc[nH]2)c1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[#7;a:4]1:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1>>[#7;a:9]:[c:10](-[CH;D3;+0:1](-[C:2]-[C:3])-[c;H0;D3;+0:8]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:1):[c:11] | 45 | [{"value": 45.0, "product": "N1C(=CC=C1)C(CCC)C=1NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared as described in example 2/4, reacting the pyrrole derivative with butyraldehyde. Yield 45%.
Conditions: See reaction.notes.procedure_details.
Workup: This was prepared | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1cc[nH]c1 | c1cc[nH]c1.c1cc[nH]c1 | c1cc[nH]c1.c1cc[nH]c1 | null | null | null | null | CCCC=O.c1cc[nH]c1>>CCCC(c1ccc[nH]1)c1ccc[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce562329315947d4a7330023ab1ce86c | O.c1ccc2[nH]ccc2c1>>O=C(O)CCC(n1ccc2ccccc21)n1ccc2ccccc21 | O.N1C=CC2=CC=CC=C12>>N1(C=CC2=CC=CC=C12)C(CCC(=O)O)N1C=CC2=CC=CC=C12 | [OH2:1].[cH:2]1[cH:11][c:10]2[cH:9][cH:8][nH:7][c:15]2[cH:14][cH:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH:6]([n:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12)[n:16]1[cH:17][cH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12 | O.c1ccc2[nH]ccc2c1 | O=C(O)CCC(n1ccc2ccccc21)n1ccc2ccccc21 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | be0a6a5708f4255fc1dc22abadb70851316780d90ed7242acaafd2618f261df5 | 9c7315ed19eeb7fef800780efa97a4613aacc14e062139968377b759809e441c | c1ccc2c(c1)ccn2Cn1ccc2ccccc21 | [OH2;D0;+0:1].[c:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]2:[c:7]:[c:8]:[nH;D2;+0:9]:[c:10]:1:2>>[#7;a:11]-[C:12](-[C:13]-[C:14]-[C;H0;D3;+0:4](-[O;D1;H1:15])=[O;H0;D1;+0:1])-[n;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]2:[cH;D2;+0:5]:[c:16]:[cH;D2;+0:3]:[c:2]:[c:10]:2:1 | null | [] | 35 | CELSIUS | 24 | HOUR | 282 mg of indole (2.4 mmol) were dissolved in 10 ml of CH3OH and 5 ml of H2O; 102 mg of semisuccinic aldehyde (1 mmol) and 240 mg of dysprosium triflate-(CF3SO3)3Dy-(0.393 mmol) were added. The resulting solution was stirred at 35° C. for 24 hours. At the end of that period the methanol was removed under vacuum and the... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | Other | CO | 35 | 24 | O.c1ccc2[nH]ccc2c1>CO>O=C(O)CCC(n1ccc2ccccc21)n1ccc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-21f8ef08222e47529862c9541bf0a48e | COC1CCCO1.c1ccc2[nH]ccc2c1>>OCCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12 | N1C=CC2=CC=CC=C12.COC1OCCC1>>N1C=C(C2=CC=CC=C12)C(CCCO)C1=CNC2=CC=CC=C12 | O1[CH:18]([O:1][CH3:2])[CH2:19][CH2:20][CH2:21]1.[cH:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[OH:1][CH2:2][CH2:3][CH2:4][CH:5]([c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)[c:15]1[cH:16][nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12 | COC1CCCO1.c1ccc2[nH]ccc2c1 | OCCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0579d4344dbff33158f2416531f0c0c5490807d596e12ff564f95d1492238351 | f4039f6137c58f023c0dcbef20c5fb1b1eb5a4818bb4583d7316df6dacf02876 | c1ccc2c(Cc3c[nH]c4ccccc34)c[nH]c2c1 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[CH;D3;+0:3]1-O-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-1.[c:7]:[c:8]1:[#7;a:9]:[c:10]:[cH;D2;+0:11]:[c:12]:1:[c:13]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[C:14]-[C:15]-[C:16](-[c:17]1:[c:18]:[#7;a:19]:[c;H0;D3;+0:3]2:[cH;D2;+0:6]:[cH;D2;+0:5]:[cH;D2;+0:4]:[c:20]:[c:21]:1:2)-[c;H0;D3;+0:11]1:[c:10]... | null | [] | null | null | null | null | The compound was prepared in the same way as described in example 2/4, starting from indole and 2-methoxy-tetrahydrofuran.
Conditions: See reaction.notes.procedure_details.
Workup: The compound was prepared in the same way | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOC1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | null | null | null | null | COC1CCCO1.c1ccc2[nH]ccc2c1>>OCCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4dd0bc4fe8c64d9e8f8801e446e2f232 | CCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12.ClCc1ccccc1>>CCCC(c1cn(Cc2ccccc2)c2ccccc12)c1cn(Cc2ccccc2)c2ccccc12 | N1C=C(C2=CC=CC=C12)C(CCC)C1=CNC2=CC=CC=C12.C(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)N1C=C(C2=CC=CC=C12)C(CCC)C1=CN(C2=CC=CC=C12)CC1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][nH:7][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12)[c:21]1[cH:22][nH:23][c:31]2[cH:32][cH:8][cH:34][cH:35][c:36]12.Cl[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][n:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][... | CCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12.ClCc1ccccc1 | CCCC(c1cn(Cc2ccccc2)c2ccccc12)c1cn(Cc2ccccc2)c2ccccc12 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | O.C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | a81b71b4c4c3b573719981f1d2cd0559bc3698c6db2b57a3252a026744953a32 | bba2945f18bbb88e48f2c5641704d2237fa5a07400e9b29e8d58901a4d971dcb | c1ccc(Cn2cc(Cc3cn(Cc4ccccc4)c4ccccc34)c3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]1:[c:6]:[nH;D2;+0:7]:[c:8]2:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[c:13]:1:2.[c:14]:[c:15]1:[c:16]:[c:17]:[c:18]:[nH;D2;+0:19]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:13]2:[c:12]:[cH;D2;+0:11]:[c:20]:[cH;D2;+0:9]:[c:8]:2:1):[c:4].[c:21]:[c:22](-[C... | 78 | [{"value": 78.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC=CC=C12)C(CCC)C1=CN(C2=CC=CC=C12)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | ST 1385 1,1-di-indol-3-yl-butane, 290 mg (1 mmol), was thoroughly mixed and blended with potassium tertbutylate (280 mg) and tetrabutylammonium bromide (20 mg). The mixture thus obtained was held under ultrasonic stirring at ambient temperature. 640 mg (5 mmol) of benzylchloride at 0° C. were then added and the ultraso... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1c[nH]c2ccccc12.c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12.c1ccccc1.c1c[nH]c2ccccc12 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.C(Cl)(Cl)Cl | null | 2 | CCCC(c1c[nH]c2ccccc12)c1c[nH]c2ccccc12.ClCc1ccccc1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.C(Cl)(Cl)Cl>CCCC(c1cn(Cc2ccccc2)c2ccccc12)c1cn(Cc2ccccc2)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-053aef3bb4e14e958a06b1ca6a830675 | Cc1cccc(O)c1[N+](=O)[O-].ClCCN1CCCC1>>Cc1cccc(OCCN2CCCC2)c1[N+](=O)[O-] | Cl.ClCCN1CCCC1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].CC=1C(=C(C=CC1)O)[N+](=O)[O-].Cl.ClCCN1CCCC1.C([O-])([O-])=O.[K+].[K+]>>CC=1C(=C(OCCN2CCCC2)C=CC1)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:7])[c:15]1[N+:16](=[O:17])[O-:18].Cl[CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15]1[N+:16](=[O:17])[O-:18] | Cc1cccc(O)c1[N+](=O)[O-].ClCCN1CCCC1 | Cc1cccc(OCCN2CCCC2)c1[N+](=O)[O-] | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCN2CCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 69 | [{"value": 69.0, "product": "CC=1C(=C(OCCN2CCCC2)C=CC1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": "CC=1C(=C(OCCN2CCCC2)C=CC1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Potassium carbonate (34.9 g., 252 mmol) and sodium iodide (1.0 g., 6.5 mmol) were added to a solution of 3-methyl-2-nitrophenol (10 g., 65.3 mmol). With stirring, 1-(2-chloroethyl)-pyrrolidine hydrochloride (16.65 g., 98 mmol) was added portion-wise to the solution. The reaction mixture was refluxed for 15 hours, at wh... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]C1 | HCl | null | null | null | Cc1cccc(O)c1[N+](=O)[O-].ClCCN1CCCC1>>Cc1cccc(OCCN2CCCC2)c1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d630b16d159d461ab24d52bd054d2105 | CN(C)CCOc1cccc2cc[nH]c12.Cc1cccc(OCCN2CCCC2)c1[N+](=O)[O-]>>c1cc(OCCN2CCCC2)c2[nH]ccc2c1 | CN(CCOC1=C(C(=CC=C1)C)[N+](=O)[O-])C.CC=1C(=C(OCCN2CCCC2)C=CC1)[N+](=O)[O-].N1C=CC2=CC=CC(=C12)OCCN(C)C>>N1(CCCC1)CCOC=1C=CC=C2C=CNC12 | CN(C)CCOc1cccc2c1[nH][cH:14][cH:15]2.C[c:16]1[c:12]([N+:13](=O)[O-])[c:3]([O:4][CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:2][cH:1][cH:17]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[c:12]2[nH:13][cH:14][cH:15][c:16]2[cH:17]1 | CN(C)CCOc1cccc2cc[nH]c12.Cc1cccc(OCCN2CCCC2)c1[N+](=O)[O-] | c1cc(OCCN2CCCC2)c2[nH]ccc2c1 | null | null | null | Functional Group Interconversion | OtherReaction | 12424c63d3fa01c4059a4bb31ed39ed8757d1e260dc5a3bac3db3fa104cc1975 | 8c13929085ad4895d58ee34dc1e3d96ab276ec2f67337a1d5210ac6e1bd98088 | c1cc(OCCN2CCCC2)c2[nH]ccc2c1 | C-N(-C)-C-C-O-c1:c:c:c:c2:[cH;D2;+0:1]:[cH;D2;+0:2]:[nH]:c:1:2.C-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[N+;H0;D3:7](=O)-[O-]):[c:8]>>[c:5]:[c:4]:[c;H0;D3;+0:3]1:[cH;D2;+0:1]:[cH;D2;+0:2]:[nH;D2;+0:7]:[c:6]:1:[c:8] | null | [] | null | null | null | null | The following compound was prepared in a similar fashion, starting with dimethyl-[2-(3-methyl-2-nitro-phenoxy)-ethyl]-amine rather than 1-[2-(3-methyl-2-nitrophenoxy)-ethyl]-pyrrolidine: [2-(1H-indol-7-yloxy)-ethyl]-dimethyl-amine (69%), MS: 205 (M+H)+
Conditions: See reaction.notes.procedure_details.
Workup: The follo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group.Tertiary amine | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1 | C1CC[NH]C1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CN(C)CCOc1cccc2cc[nH]c12.Cc1cccc(OCCN2CCCC2)c1[N+](=O)[O-]>>c1cc(OCCN2CCCC2)c2[nH]ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-657f79367abc4069a1261c2d77576d05 | CI.CN(CCOc1cccc2c(S(=O)(=O)c3ccccc3F)c[nH]c12)C(=O)OC(C)(C)C>>CN(CCOc1cccc2c(S(=O)(=O)c3ccccc3F)cn(C)c12)C(=O)OC(C)(C)C | C(C)(C)(C)OC(N(C)CCOC=1C=CC=C2C(=CNC12)S(=O)(=O)C1=C(C=CC=C1)F)=O.[H-].[Na+].CI>>C(C)(C)(C)OC(N(C)CCOC=1C=CC=C2C(=CN(C12)C)S(=O)(=O)C1=C(C=CC=C1)F)=O | I[CH3:24].[CH3:1][N:2]([CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]([S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[F:21])[cH:22][nH:23][c:25]12)[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32]>>[CH3:1][N:2]([CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]([S:12](=[O:13])(=... | CI.CN(CCOc1cccc2c(S(=O)(=O)c3ccccc3F)c[nH]c12)C(=O)OC(C)(C)C | CN(CCOc1cccc2c(S(=O)(=O)c3ccccc3F)cn(C)c12)C(=O)OC(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5ce73e9bd608d5491381e563c654ad03f655de6d7aa46423d6263e854c49919a | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=S(=O)(c1ccccc1)c1c[nH]c2ccccc12 | 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 | 10 | MINUTE | A dry 25 mL flask equipped with a magnetic stirrer was charged with {2-[3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester (0.116 g., 0.258 mmol) and dimethylformamide (5 mL.) This solution was treated with sodium hydride (0.011 g. of 60% suspension in mineral oil, 0.284 mmol) a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HI | CN(C=O)C | null | 0.166667 | CI.CN(CCOc1cccc2c(S(=O)(=O)c3ccccc3F)c[nH]c12)C(=O)OC(C)(C)C>CN(C=O)C>CN(CCOc1cccc2c(S(=O)(=O)c3ccccc3F)cn(C)c12)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e9e8d5c94114eeeb2ac26b063c4d5b9 | CC(C)(C)OC(=O)N1CC(COc2cccc3[nH]ccc23)C1>>CN(CCOc1cccc2[nH]ccc12)C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1CC(C1)CO.C(C)(C)(C)OC(=O)N1CC(C1)COC1=C2C=CNC2=CC=C1>>C(C)(C)(C)OC(N(C)CCOC1=C2C=CNC2=CC=C1)=O | C1[N:2]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:1][CH:3]1[CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[nH:11][cH:12][cH:13][c:14]12>>[CH3:1][N:2]([CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[nH:11][cH:12][cH:13][c:14]12)[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21] | CC(C)(C)OC(=O)N1CC(COc2cccc3[nH]ccc23)C1 | CN(CCOc1cccc2[nH]ccc12)C(=O)OC(C)(C)C | null | null | null | Miscellaneous | OtherReaction | 7e6a6565c453df5d5d90babf757b6ca136771d4877777d8a0e0fb7358084654f | b932663ddba91899c323dafb4072eae107b143d8b23ee72dc5710c79986212ad | c1ccc2[nH]ccc2c1 | [#8:1]-[C:2]-[CH;D3;+0:3]1-C-[N;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[CH2;D2;+0:12]-1>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:12])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11] | null | [] | null | null | null | null | In a similar manner, using 3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester in place of (2-hydroxy-ethyl)-methyl-carbamic acid tert-butyl ester, 3-(1H-Indol-4-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester was prepared, (25%), (M−H)−=301.
Conditions: See reaction.notes.procedure_details.
Workup: ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester | Carbamic ester | C1C[NH]C1 | null | c1ccc2[nH]ccc2c1 | Other | null | null | null | CC(C)(C)OC(=O)N1CC(COc2cccc3[nH]ccc23)C1>>CN(CCOc1cccc2[nH]ccc12)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0598c4a6efe64da582219cf0fd57ed5b | CN(CCOc1cccc2c1cc(S(=O)(=O)c1ccccc1)n2C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>CNCCOc1cccc2[nH]c(S(=O)(=O)c3ccccc3)cc12 | C(C)(C)(C)OC(=O)N1C(=CC2=C(C=CC=C12)OCCN(C)C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1.Cl>>Cl.C1(=CC=CC=C1)S(=O)(=O)C=1NC2=CC=CC(=C2C1)OCCNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11](C(=O)OC(C)(C)C)[c:12]([S:13](=[O:14])(=[O:15])[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22][c:23]12>>[CH3:1][NH:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[nH:11][c:12]([S:13](=[O:14])(=[O:15])[c:16]3[cH:17][cH:18][cH:19... | CN(CCOc1cccc2c1cc(S(=O)(=O)c1ccccc1)n2C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | CNCCOc1cccc2[nH]c(S(=O)(=O)c3ccccc3)cc12 | null | null | CCO | Reduction | OtherReaction | e71913f257fed84ef2af126ddaecf582cb32eea15a3c3c94fef05ab526c72196 | b6e7823586033bfbc03f4d0c8dc7543754c419d00fed6ec047b5fd9adf5eea30 | O=S(=O)(c1ccccc1)c1cc2ccccc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:5]1:[c:6](:[c:7]):[c:8]:[c:9]:[c:10]:1-[#16:11]>>[#16:11]-[c:10]1:[c:9]:[c:8]:[c:6](:[c:7]):[nH;D2;+0:5]:1.[C:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | null | [] | 100 | CELSIUS | null | null | 2-Benzenesulfonyl-4-[2-(tert-butoxycarbonyl-methyl-amino)-ethoxy]-indole-1-carboxylic acid tert-butyl ester (0.250 g., 0.5 mmol) from Step 3 was dissolved in 5 mL EtOH. To this solution was added 1 mL of 2M ethanolic hydrogen chloride solution. The reaction mixture was heated at 100° C. for 35 minutes. Upon cooling to ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine | c1cc2ccccc2[nH]1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | CCO | 100 | null | CN(CCOc1cccc2c1cc(S(=O)(=O)c1ccccc1)n2C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>CCO>CNCCOc1cccc2[nH]c(S(=O)(=O)c3ccccc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-97136cb279ec42c48c1676e51c7624a8 | CN(CCOc1cccc2cc(S(=O)(=O)c3ccccc3)n(C(=O)OC(C)(C)C)c12)C(=O)OC(C)(C)C>>CNCCOc1cccc2cc(S(=O)(=O)c3ccccc3)[nH]c12 | C(C)(C)(C)OC(=O)N1C(=CC2=CC=CC(=C12)OCCN(C)C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1.Cl>>Cl.C1(=CC=CC=C1)S(=O)(=O)C=1NC2=C(C=CC=C2C1)OCCNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][c:12]([S:13](=[O:14])(=[O:15])[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[n:22](C(=O)OC(C)(C)C)[c:23]12>>[CH3:1][NH:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][c:12]([S:13](=[O:14])(=[O:15])[c:16]3[cH:17][cH:18][cH:19... | CN(CCOc1cccc2cc(S(=O)(=O)c3ccccc3)n(C(=O)OC(C)(C)C)c12)C(=O)OC(C)(C)C | CNCCOc1cccc2cc(S(=O)(=O)c3ccccc3)[nH]c12 | null | null | CCO | Reduction | OtherReaction | e71913f257fed84ef2af126ddaecf582cb32eea15a3c3c94fef05ab526c72196 | b6e7823586033bfbc03f4d0c8dc7543754c419d00fed6ec047b5fd9adf5eea30 | O=S(=O)(c1ccccc1)c1cc2ccccc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:5]1:[c:6](-[#16:7]):[c:8]:[c:9]:[c:10]:1:[c:11]>>[#16:7]-[c:6]1:[c:8]:[c:9]:[c:10](:[c:11]):[nH;D2;+0:5]:1.[C:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | null | [] | 100 | CELSIUS | null | null | 2-Benzenesulfonyl-7-[2-(tert-butoxycarbonyl-methyl-amino)-ethoxy]-indole-1-carboxylic acid tert-butyl ester (0.230 g., 0.43 mmol) from the above step was dissolved in 5 mL EtOH. To this solution was added 1 mL of 2M ethanolic hydrogen chloride solution. The reaction mixture was heated at 100° C. for 35 minutes. Upon co... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine | c1cc2ccccc2[nH]1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | CCO | 100 | null | CN(CCOc1cccc2cc(S(=O)(=O)c3ccccc3)n(C(=O)OC(C)(C)C)c12)C(=O)OC(C)(C)C>CCO>CNCCOc1cccc2cc(S(=O)(=O)c3ccccc3)[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-586c518b04a74c998bdaf509414209bb | N#CCBr.Oc1cccc2cc[nH]c12>>N#CCOc1cccc2cc[nH]c12 | BrCC#N.OC=1C=CC=C2C=CNC12.C([O-])([O-])=O.[K+].[K+]>>N1C=CC2=CC=CC(=C12)OCC#N | Br[CH2:3][C:2]#[N:1].[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][nH:12][c:13]12>>[N:1]#[C:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][nH:12][c:13]12 | N#CCBr.Oc1cccc2cc[nH]c12 | N#CCOc1cccc2cc[nH]c12 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10] | null | [] | 0 | CELSIUS | 3 | HOUR | In a 100 mL roundbottom flask equipped with a magnetic stirrer and rubber septum, 7-hydroxy-1H-indole (1.66 g., 12.48 mmol) was dissolved 50 mL anhydrous acetonitrile. The flask was charged with potassium carbonate (6.88 g., 49.9 mmol) and cooled to 0° C. While stirring, bromoacetonitrile (1.64 g., 13.73 mmol) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1 | HBr | C(C)#N | 0 | 3 | N#CCBr.Oc1cccc2cc[nH]c12>C(C)#N>N#CCOc1cccc2cc[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28ef4f87f29444f4ab29c44206c85e6f | NCCOc1cccc2c(S(=O)(=O)c3ccccc3F)c[nH]c12>>NCCOc1cccc2c(S(=O)(=O)c3ccccc3F)c[nH]c12 | O.O.O.O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Na+].[Na+].FC1=C(C=CC=C1)S(=O)(=O)C1=CNC2=C(C=CC=C12)OCCN.Cl>>Cl.FC1=C(C=CC=C1)S(=O)(=O)C1=CNC2=C(C=CC=C12)OCCN | [NH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]([S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[F:21])[cH:22][nH:23][c:24]12>>[NH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]([S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[F:21])[cH:22][nH:23][c:24]12 | NCCOc1cccc2c(S(=O)(=O)c3ccccc3F)c[nH]c12 | NCCOc1cccc2c(S(=O)(=O)c3ccccc3F)c[nH]c12 | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=S(=O)(c1ccccc1)c1c[nH]c2ccccc12 | null | 11 | [{"value": 11.0, "product": "Cl.FC1=C(C=CC=C1)S(=O)(=O)C1=CNC2=C(C=CC=C12)OCCN", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A dry 25 mL roundbottom flask was equipped with a magnetic stirrer and purged with argon gas. To this was added via syringe a solution of [3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-acetonitrile in 10 mL of anhydrous THF. The flask was cooled to 0° C. and lithium aluminum hydride solution was added (1 mL of 1M solu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | null | C(C)O | 0 | 1 | NCCOc1cccc2c(S(=O)(=O)c3ccccc3F)c[nH]c12>C(C)O>NCCOc1cccc2c(S(=O)(=O)c3ccccc3F)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c726936bb48143acb2070697d2b01b54 | NS(=O)(=O)c1ccc(Br)s1>>N#Cc1ccc(S(N)(=O)=O)s1 | CO.CN(C=O)C.O.C(C)(=O)OCC.BrC1=CC=C(S1)S(=O)(=O)N.CN(C=O)C>>C(#N)C1=CC=C(S1)S(=O)(=O)N | Br[c:3]1[cH:4][cH:5][c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[s:11]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[s:11]1 | NS(=O)(=O)c1ccc(Br)s1 | N#Cc1ccc(S(N)(=O)=O)s1 | null | [C-]#N.[Zn+2].[C-]#N.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 | C(Cl)Cl | Miscellaneous | OtherReaction | ebc2e53b7bb2dea43338a6ebf76eca4e26da1c045bb86707697af7150e28603d | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccsc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | null | null | 15 | MINUTE | A mixture of 5-bromothiophene-2-sulfonamide (0.50 g, 2.1 mmol), zinc cyanide (0.25 g, 2.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.072 g, 0.06 mmol) in dimethylformamide (5 mL, anhydrous) is placed under microwave radiation (under nitrogen atmosphere, 160° C.) for 15 min. Thin layer chromatography (5% methyl ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccsc1 | c1ccsc1 | c1ccsc1 | Br- | [C-]#N.[Zn+2].[C-]#N.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.C(Cl)Cl | null | 0.25 | NS(=O)(=O)c1ccc(Br)s1>[C-]#N.[Zn+2].[C-]#N.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.C(Cl)Cl>N#Cc1ccc(S(N)(=O)=O)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b3ef08a6ec846058fe20b3dbccc2c1d | NS(=O)(=O)c1ccc(Br)s1.[C]=O>>COC(=O)c1ccc(S(N)(=O)=O)s1 | [C]=O.BrC1=CC=C(S1)S(=O)(=O)N.C(C)N(CC)CC.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC>>COC(=O)C1=CC=C(S1)S(=O)(=O)N | Br[c:5]1[cH:6][cH:7][c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[s:13]1.[C:3]=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[s:13]1 | NS(=O)(=O)c1ccc(Br)s1.[C]=O | COC(=O)c1ccc(S(N)(=O)=O)s1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CO.CN(C=O)C.[Cl-].[Na+].O | Acylation | OtherReaction | 4a22c433c553169ad2d2a5923b627757ce76160edc71987c02daeeccd0e27f17 | 843b64a5a526f70107d024a7003b94aa750190d2759e9e4e7ac8f05f2eb068bc | c1ccsc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.[C;H0;D1;+0:6]=[O;D1;H0:7]>>[C;D1;H3:8]-[#8:9]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | 100 | CELSIUS | 8 | HOUR | A mixture of 5-bromothiophene-2-sulfonamide (0.50 g, 2.1 mmol), triethyl amine (1 mL), methanol (1 mL), palladium acetate (0.046 g, 2.1 mmol) and 1,3-bis(diphenylphosphino) propane (0.085 g, 2.1 mmol) (addition in that order) in dimethylformamide (5 mL, anhydrous) is saturated with carbon monoxide gas, at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ester | c1ccsc1 | c1ccsc1 | c1ccsc1 | Br- | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CO.CN(C=O)C.[Cl-].[Na+].O | 100 | 8 | NS(=O)(=O)c1ccc(Br)s1.[C]=O>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CO.CN(C=O)C.[Cl-].[Na+].O>COC(=O)c1ccc(S(N)(=O)=O)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ee96dca7353343b0ab451e1a1c0600f7 | NS(=O)(=O)c1cc(Cl)c(Br)s1>>NS(=O)(=O)c1cc(Cl)cs1 | BrC1=C(C=C(S1)S(=O)(=O)N)Cl>>ClC=1C=C(SC1)S(=O)(=O)N | Br[c:9]1[c:7]([Cl:8])[cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[s:10]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][s:10]1 | NS(=O)(=O)c1cc(Cl)c(Br)s1 | NS(=O)(=O)c1cc(Cl)cs1 | null | [Zn] | CC(=O)O | Functional Group Interconversion | Aromatic dehalogenation | 305afd15d586f55c801d6d4acac09c00bdce7795c11721d329be09a54571e3e8 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccsc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[Cl;D1;H0:6]>>[Cl;D1;H0:6]-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[cH;D2;+0:1]:1 | 52 | [{"value": 52.0, "product": "ClC=1C=C(SC1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.2, "product": "ClC=1C=C(SC1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 6 | HOUR | To a stirred solution of 5-bromo-4-chlorothiophene-2-sulfonamide (2.4 g, 8.7 mmol) in AcOH (20 mL) is added zinc dust (1.7 g, 26.0 mmol). The reaction mixture is heated to 120° C. for 6 hr. After 6 hr, the mixture is filtered and neutralized with 1 M NaOH. The aqueous layer is extracted with EtOAc (2×100 mL). The combi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccsc1 | c1ccsc1 | c1ccsc1 | Br- | [Zn].CC(=O)O | 120 | 6 | NS(=O)(=O)c1cc(Cl)c(Br)s1>[Zn].CC(=O)O>NS(=O)(=O)c1cc(Cl)cs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d567173a966040fe8fce61a1b01b4a96 | Cc1cc(S(N)(=O)=O)sc1Br>>Cc1csc(S(N)(=O)=O)c1 | BrC1=C(C=C(S1)S(=O)(=O)N)C>>CC=1C=C(SC1)S(=O)(=O)N | Br[c:3]1[c:2]([CH3:1])[cH:10][c:5]([S:6]([NH2:7])(=[O:8])=[O:9])[s:4]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([S:6]([NH2:7])(=[O:8])=[O:9])[cH:10]1 | Cc1cc(S(N)(=O)=O)sc1Br | Cc1csc(S(N)(=O)=O)c1 | null | [Zn] | CC(=O)O | Functional Group Interconversion | Aromatic dehalogenation | 305afd15d586f55c801d6d4acac09c00bdce7795c11721d329be09a54571e3e8 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccsc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[C;D1;H3:6]>>[C;D1;H3:6]-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[cH;D2;+0:1]:1 | 43 | [{"value": 43.0, "product": "CC=1C=C(SC1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.0, "product": "CC=1C=C(SC1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 5-bromo-4-methylthiophene-2-sulfonamide (3.1 g, 12.1 mmol) in AcOH (30 mL) is added zinc dust (2.4 g, 36.2 mmol). The reaction mixture is heated to reflux for 8 hr. After 8 hr, the reaction mixture is cooled and filtered. The filtrate is neutralized with 1 M NaOH. The aqueous layer is extracted... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccsc1 | c1ccsc1 | c1ccsc1 | Br- | [Zn].CC(=O)O | null | 8 | Cc1cc(S(N)(=O)=O)sc1Br>[Zn].CC(=O)O>Cc1csc(S(N)(=O)=O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-565e2ecce6004964ad51bb958a449fdc | COc1ccsc1.C[Si](C)(C)Cl>>COc1ccsc1[Si](C)(C)C | [Li]CCCC.COC1=CSC=C1.Cl[Si](C)(C)C>>C[Si](C=1SC=CC1OC)(C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][s:6][cH:7]1.Cl[Si:8]([CH3:9])([CH3:10])[CH3:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][s:6][c:7]1[Si:8]([CH3:9])([CH3:10])[CH3:11] | COc1ccsc1.C[Si](C)(C)Cl | COc1ccsc1[Si](C)(C)C | null | null | CCOCC | Functional Group Interconversion | OtherReaction | 9d3a5d1aca09168804224649157f4cdeee866ecdd1eb4932b5bd9bc687e334ae | 62b25486659a0c3b8981491307676661488416039e4a601c8996c7216be92cf1 | c1ccsc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[#8:5]-[c:6]1:[c:7]:[c:8]:[#16;a:9]:[cH;D2;+0:10]:1>>[#8:5]-[c:6]1:[c:7]:[c:8]:[#16;a:9]:[c;H0;D3;+0:10]:1-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4] | 82 | [{"value": 82.0, "product": "C[Si](C=1SC=CC1OC)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.6, "product": "C[Si](C=1SC=CC1OC)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 2 | HOUR | A solution of n-BuLi (19.7 mL of 1.6 M in hexanes, 31.5 mmol) is added dropwise to a solution of 3-methoxythiophene (3.0 g, 26.3 mmol) in anhydrous Et2O (20 mL) under nitrogen at −70° C. The mixture is stirred at −70° C. for 2 hr. Chlorotrimethylsilane (4.5 mL, 35.4 mmol) is added slowly to the solution. The mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1ccsc1 | c1ccsc1 | c1ccsc1 | HCl | CCOCC | -70 | 2 | COc1ccsc1.C[Si](C)(C)Cl>CCOCC>COc1ccsc1[Si](C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4011bed5f5294dad8742b47fef93d11e | COc1cc(S(N)(=O)=O)sc1[Si](C)(C)C>>COc1csc(S(N)(=O)=O)c1 | C[Si](C1=C(C=C(S1)S(=O)(=O)N)OC)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>COC=1C=C(SC1)S(=O)(=O)N | C[Si](C)(C)[c:4]1[c:3]([O:2][CH3:1])[cH:11][c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[s:5]1>>[CH3:1][O:2][c:3]1[cH:4][s:5][c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[cH:11]1 | COc1cc(S(N)(=O)=O)sc1[Si](C)(C)C | COc1csc(S(N)(=O)=O)c1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | fb103db3c69bbb9797704a2b619962ad5a7046c2eac756eb173e3698fc27e14b | dc52a720480da1d65217db7d5178c684d09e72e99cbbe1f9f67cca818c9ff2e9 | c1ccsc1 | C-[Si](-C)(-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[#8:6]>>[#8:6]-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[cH;D2;+0:1]:1 | 86 | [{"value": 86.0, "product": "COC=1C=C(SC1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.7, "product": "COC=1C=C(SC1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 5-trimethylsilyl-4-methoxythiophene-2-sulfonamide (770 mg, 2.90 mmol) in THF (10 mL) is added a solution of tetra-butylammonium fluoride (17.4 mL of 1 M in THF, 17.4 mmol). The reaction mixture is stirred at room temperature for 2 hr. The THF is removed under reduced pressure. The residue is dissolved ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1ccsc1 | c1ccsc1 | c1ccsc1 | Other | C1CCOC1 | null | 2 | COc1cc(S(N)(=O)=O)sc1[Si](C)(C)C>C1CCOC1>COc1csc(S(N)(=O)=O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-691061cfa6dd4a19863f6daf18e6a0b4 | COc1csc(S(N)(=O)=O)c1.O=C1CCC(=O)N1Br>>COc1cc(S(N)(=O)=O)sc1Br | COC=1C=C(SC1)S(=O)(=O)N.BrN1C(CCC1=O)=O>>BrC1=C(C=C(S1)S(=O)(=O)N)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([S:6]([NH2:7])(=[O:8])=[O:9])[s:10][cH:11]1.O=C1CCC(=O)N1[Br:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([S:6]([NH2:7])(=[O:8])=[O:9])[s:10][c:11]1[Br:12] | COc1csc(S(N)(=O)=O)c1.O=C1CCC(=O)N1Br | COc1cc(S(N)(=O)=O)sc1Br | null | null | C(Cl)Cl | Functional Group Interconversion | Bromination | a42d5393618d10b862dd7bd471fa3f4459c31017c8714cafb4e591f8ed4a8052 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccsc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[cH;D2;+0:7]:1>>[#8:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c;H0;D3;+0:7]:1-[Br;H0;D1;+0:1] | 82.1 | [{"value": 82.0, "product": "BrC1=C(C=C(S1)S(=O)(=O)N)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.1, "product": "BrC1=C(C=C(S1)S(=O)(=O)N)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 7 | HOUR | To a solution of 4-methoxythiophene-2-sulfonamide (240 mg, 1.24 mmol) in CH2Cl2 (40 mL) is added N-bromosuccinimide (287 mg, 1.61 mmol). The reaction mixture is stirred at 0° C. for 7 hr. After 7 hr, the reaction mixture is diluted with CH2Cl2 (150 mL). The organic layer is washed with brine then dried (Na2SO4), filter... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccsc1.C1CCNC1 | c1ccsc1 | c1ccsc1 | HO- | C(Cl)Cl | 0 | 7 | COc1csc(S(N)(=O)=O)c1.O=C1CCC(=O)N1Br>C(Cl)Cl>COc1cc(S(N)(=O)=O)sc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9191d766b42f4cd196abeaea614de401 | CSc1ccsc1.C[Si](C)(C)Cl>>CSc1ccsc1[Si](C)(C)C | [Li]CCCC.CSC1=CSC=C1.Cl[Si](C)(C)C>>C[Si](C=1SC=CC1SC)(C)C | [CH3:1][S:2][c:3]1[cH:4][cH:5][s:6][cH:7]1.Cl[Si:8]([CH3:9])([CH3:10])[CH3:11]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][s:6][c:7]1[Si:8]([CH3:9])([CH3:10])[CH3:11] | CSc1ccsc1.C[Si](C)(C)Cl | CSc1ccsc1[Si](C)(C)C | null | null | CCOCC | Functional Group Interconversion | OtherReaction | 9d3a5d1aca09168804224649157f4cdeee866ecdd1eb4932b5bd9bc687e334ae | 62b25486659a0c3b8981491307676661488416039e4a601c8996c7216be92cf1 | c1ccsc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[#16:5]-[c:6]1:[c:7]:[c:8]:[#16;a:9]:[cH;D2;+0:10]:1>>[#16:5]-[c:6]1:[c:7]:[c:8]:[#16;a:9]:[c;H0;D3;+0:10]:1-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4] | 48 | [{"value": 48.0, "product": "C[Si](C=1SC=CC1SC)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 2 | HOUR | A solution of n-BuLi (5.3 mL of 1.6 M in hexanes, 8.5 mmol) is added dropwise to a solution of 3-methylsulfanylthiophene (1.0 g, 7.7 mmol) in anhydrous Et2O (8 mL) under nitrogen at −70° C. The mixture is stirred at −70° C. for 2 hr. Chlorotrimethylsilane (1.5 mL) is added slowly to the reaction mixture. The mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1ccsc1 | c1ccsc1 | c1ccsc1 | HCl | CCOCC | -70 | 2 | CSc1ccsc1.C[Si](C)(C)Cl>CCOCC>CSc1ccsc1[Si](C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a67ac309ad074910a843d2a272c82903 | CSc1cc(S(N)(=O)=O)sc1[Si](C)(C)C>>CSc1csc(S(N)(=O)=O)c1 | C[Si](C1=C(C=C(S1)S(=O)(=O)N)SC)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>CSC=1C=C(SC1)S(=O)(=O)N | C[Si](C)(C)[c:4]1[c:3]([S:2][CH3:1])[cH:11][c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[s:5]1>>[CH3:1][S:2][c:3]1[cH:4][s:5][c:6]([S:7]([NH2:8])(=[O:9])=[O:10])[cH:11]1 | CSc1cc(S(N)(=O)=O)sc1[Si](C)(C)C | CSc1csc(S(N)(=O)=O)c1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | fb103db3c69bbb9797704a2b619962ad5a7046c2eac756eb173e3698fc27e14b | dc52a720480da1d65217db7d5178c684d09e72e99cbbe1f9f67cca818c9ff2e9 | c1ccsc1 | C-[Si](-C)(-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[#16:6]>>[#16:6]-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[cH;D2;+0:1]:1 | 82 | [{"value": 82.0, "product": "CSC=1C=C(SC1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "CSC=1C=C(SC1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 5-trimethylsilyl-4-methylsulfanylthiophene-2-sulfonamide (660 mg, 2.34 mmol) in THF (10 mL) is added a solution of tetra-butylammonium fluoride (14.0 mL of 1 M in THF, 14.0 mmol). The reaction mixture is stirred at room temperature for 3 hr. The THF is removed under reduced pressure and the residue is ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1ccsc1 | c1ccsc1 | c1ccsc1 | Other | C1CCOC1 | null | 3 | CSc1cc(S(N)(=O)=O)sc1[Si](C)(C)C>C1CCOC1>CSc1csc(S(N)(=O)=O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0942076c4c394968b6a28abbf66cf3d6 | CSc1csc(S(N)(=O)=O)c1.O=C1CCC(=O)N1Br>>CSc1cc(S(N)(=O)=O)sc1Br | CSC=1C=C(SC1)S(=O)(=O)N.BrN1C(CCC1=O)=O.[OH-].[Na+]>>BrC1=C(C=C(S1)S(=O)(=O)N)SC | [CH3:1][S:2][c:3]1[cH:4][c:5]([S:6]([NH2:7])(=[O:8])=[O:9])[s:10][cH:11]1.O=C1CCC(=O)N1[Br:12]>>[CH3:1][S:2][c:3]1[cH:4][c:5]([S:6]([NH2:7])(=[O:8])=[O:9])[s:10][c:11]1[Br:12] | CSc1csc(S(N)(=O)=O)c1.O=C1CCC(=O)N1Br | CSc1cc(S(N)(=O)=O)sc1Br | null | null | C(Cl)(Cl)Cl.CC(=O)O | Functional Group Interconversion | Bromination | a42d5393618d10b862dd7bd471fa3f4459c31017c8714cafb4e591f8ed4a8052 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccsc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#16:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[cH;D2;+0:7]:1>>[#16:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c;H0;D3;+0:7]:1-[Br;H0;D1;+0:1] | 70 | [{"value": 70.0, "product": "BrC1=C(C=C(S1)S(=O)(=O)N)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.4, "product": "BrC1=C(C=C(S1)S(=O)(=O)N)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | To a solution of 4-methylsulfanylthiophene-2-sulfonamide (210 mg, 1.00 mmol) in CHCl3 (10 mL) and AcOH (10 mL) is added N-bromosuccinimide (231 mg, 1.30 mmol). The reaction mixture is stirred at room temperature for 7 hr. After 7 hr, the reaction mixture is neutralized with 1 M NaOH and the solution is extracted with E... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccsc1.C1CCNC1 | c1ccsc1 | c1ccsc1 | HO- | C(Cl)(Cl)Cl.CC(=O)O | null | 7 | CSc1csc(S(N)(=O)=O)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)Cl.CC(=O)O>CSc1cc(S(N)(=O)=O)sc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55e97c7bfb3c4a3b8e73d36580db020d | Nc1ccc(Br)cc1Br>>N#Cc1ccc(Br)cc1Br | Cl.BrC1=C(N)C=CC(=C1)Br.[Cu](C#N)C#N.C(C)(C)(C)ON=O>>BrC1=C(C#N)C=CC(=C1)Br | N[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[Br:10]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[Br:10] | Nc1ccc(Br)cc1Br | N#Cc1ccc(Br)cc1Br | null | null | CS(=O)C | Miscellaneous | OtherReaction | 803ab123dd5297cb23d9a6340952837f436e629c02fa01486d208bb7e2b4e208 | fb780e6912aa057969f5ca1e3a4b096c038904d81ac37783ac8b177057c79824 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Br;D1;H0:5]):[c:6]>>[Br;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[c:2]:[c:3] | 31 | [{"value": 31.0, "product": "BrC1=C(C#N)C=CC(=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.0, "product": "BrC1=C(C#N)C=CC(=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 1 | HOUR | Copper cyanide (2.32 g, 25.9 mmol) is added to stirred anhydrous dimethylsulfoxide (50 mL) at 60° C. to form a clear solution, followed by the addition of tert-butylnitrite (7.1 mL, 59.7 mmol) all at once. A solution of 2,4-dibromoaniline 21 (5.0 g, 19.9 mmol) in anhydrous dimethylsulfoxide (30 mL) is added dropwise, v... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CS(=O)C | 45 | 1 | Nc1ccc(Br)cc1Br>CS(=O)C>N#Cc1ccc(Br)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09dbf5b4d43440c18a10b96ec12ac8d1 | Br.Nc1cc(Cl)ccc1C(=O)O>>O=C(O)c1ccc(Cl)cc1Br | NC1=C(C(=O)O)C=CC(=C1)Cl.Br.[N+](=O)([O-])[O-].[Na+]>>BrC1=C(C(=O)O)C=CC(=C1)Cl | [BrH:11].N[c:10]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][cH:6][c:7]([Cl:8])[cH:9]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]1[Br:11] | Br.Nc1cc(Cl)ccc1C(=O)O | O=C(O)c1ccc(Cl)cc1Br | null | [Cu](Br)Br | O | Miscellaneous | OtherReaction | 976fb3f0996203ccf639edc3dd63ebf792dabe502fe07eb66206f5ee630d746b | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8].[BrH;D0;+0:9]>>[Br;H0;D1;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8] | 59 | [{"value": 59.0, "product": "BrC1=C(C(=O)O)C=CC(=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | An aqueous solution of sodium nitrate (2.21 g) in water (15 mL) is added dropwise to a stirred, ice-cooled mixture of 2-amino-4-chlorobenzoic acid (5.00 g, 29.1 mmol) and 48% hydrobromic acid (150 mL) in water (150 mL). The resultant mixture is stirred for 2 hr at 0° C. Then it is treated dropwise with an aqueous solut... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Cu](Br)Br.O | null | 8 | Br.Nc1cc(Cl)ccc1C(=O)O>[Cu](Br)Br.O>O=C(O)c1ccc(Cl)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aee51196cc95496697f04b34ba5c4da1 | CN(C)C=O.CO.Cc1ccc(Br)c(Cl)c1>>COC(=O)c1ccc(C)cc1Cl | BrC1=C(C=C(C=C1)C)Cl.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC.CO.CN(C=O)C>>ClC1=C(C(=O)OC)C=CC(=C1)C | CN(C)[CH:3]=[O:4].[CH3:1][OH:2].Br[c:5]1[cH:6][cH:7][c:8]([CH3:9])[cH:10][c:11]1[Cl:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[cH:10][c:11]1[Cl:12] | CN(C)C=O.CO.Cc1ccc(Br)c(Cl)c1 | COC(=O)c1ccc(C)cc1Cl | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | null | Acylation | OtherReaction | ba60403ad7d45c466fc5a7cbbd7ecd8e4611ae8790a58d10f5ebcfca5f732591 | 3e4a6d9d1b66fe5eba87f87fea1406f49c9bbd0c9181018bc2624480752f7ca5 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].C-N(-C)-[CH;D2;+0:7]=[O;D1;H0:8].[C;D1;H3:9]-[OH;D1;+0:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6] | 28 | [{"value": 28.0, "product": "ClC1=C(C(=O)OC)C=CC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To 4-bromo-3-chlorotoluene (4.97 g, 24.2 mmol) in dimethylformamide (25 mL) is added palladium acetate (0.54 g, 2.42 mmol), 1,3-bis(diphenylphosphino)propane (0.998 g, 2.42 mmol), triethylamine (12.5 mL) and methanol (12.5 mL). The reaction vessel is evacuated and purged three times with carbon monoxide gas. A balloon ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide.Methanol | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | 80 | null | CN(C)C=O.CO.Cc1ccc(Br)c(Cl)c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-]>COC(=O)c1ccc(C)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cea61636641643349db50d2479857ff0 | COC(=O)c1ccc(C)cc1Cl>>Cc1ccc(C(=O)O)c(Cl)c1 | ClC1=C(C(=O)OC)C=CC(=C1)C.[OH-].[Li+]>>ClC1=C(C(=O)O)C=CC(=C1)C | C[O:8][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:11][c:9]1[Cl:10])=[O:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9]([Cl:10])[cH:11]1 | COC(=O)c1ccc(C)cc1Cl | Cc1ccc(C(=O)O)c(Cl)c1 | null | null | O.O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 100 | [{"value": 100.0, "product": "ClC1=C(C(=O)O)C=CC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "ClC1=C(C(=O)O)C=CC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To methyl 2-chloro-4-methylbenzoate (1.00 g, 5.42 mmol) in tetrahydrofuran (10 mL) methyl alcohol (5 mL) and water (2.5 mL) is added 2N lithium hydroxide (8.12 mL, 16.2 mmol). The reaction mixture is heated at 50° C. for 2.5 hr, cooled to room temperature, and then quenched with 5N hydrochloric acid (3.24 mL). The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O.O1CCCC1 | 50 | null | COC(=O)c1ccc(C)cc1Cl>O.O1CCCC1>Cc1ccc(C(=O)O)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d146ffc4743f46cfb9a96289a70a2846 | CCOC(=O)CC(=O)C(F)(F)F.COS(=O)(=O)c1ccc(C)cc1>>CCOC(=O)C=C(OC)C(F)(F)F | C1(=CC=C(C=C1)S(=O)(=O)OC)C.FC(C(CC(=O)OCC)=O)(F)F.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)OC(C=C(C(F)(F)F)OC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[C:10]([F:11])([F:12])[F:13].Cc1ccc(S(=O)(=O)O[CH3:9])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]([O:8][CH3:9])[C:10]([F:11])([F:12])[F:13] | CCOC(=O)CC(=O)C(F)(F)F.COS(=O)(=O)c1ccc(C)cc1 | CCOC(=O)C=C(OC)C(F)(F)F | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 0dc58f4d3ac1f54d21a41413dfb3bbdac23e0786bbf3d7a4617d6b94a0282309 | fa98111d5b9696af827e0889b49ab9e37ed100109e38ecbec1b7162fb7d02238 | null | C-c1:c:c:c(-S(=O)(=O)-O-[CH3;D1;+0:1]):c:c:1.[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12]>>[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[C;H0;D3;+0:7](-[O;H0;D2;+0:8]-[CH3;D1;+0:1])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12] | 56 | [{"value": 56.0, "product": "C(C)OC(C=C(C(F)(F)F)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.4, "product": "C(C)OC(C=C(C(F)(F)F)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | To a solution of ethyl 4,4,4-trifluoroacetoacetate (12 mL, 82 mmol) in DMF (80 mL) is added cesium carbonate (26.4 g, 82 mmol). The reaction mixture is heated to 70° C. A solution of methyl p-toluenesulfonate (13.5 mL, 90 mmol) in DMF (30 mL) is then added dropwise during 30 min and the reaction mixture is stirred for ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ketone.Ester | Ester.Ether | c1ccccc1 | null | null | TsOH.HO- | O.CN(C)C=O | 70 | 1 | CCOC(=O)CC(=O)C(F)(F)F.COS(=O)(=O)c1ccc(C)cc1>O.CN(C)C=O>CCOC(=O)C=C(OC)C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3615251532314f45bc7131ceaf9195cd | CCOC(=O)C=C(OC)C(F)(F)F.COC(=O)CS>>COC(=O)c1sc(C(F)(F)F)cc1O | C(C)OC(C=C(C(F)(F)F)OC)=O.C(CS)(=O)OC.OS(=O)(=O)O.[OH-].[K+]>>COC(=O)C=1SC(=CC1O)C(F)(F)F | CCO[C:13]([CH:12]=[C:7](OC)[C:8]([F:9])([F:10])[F:11])=[O:14].[CH3:1][O:2][C:3](=[O:4])[CH2:5][SH:6]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]1[OH:14] | CCOC(=O)C=C(OC)C(F)(F)F.COC(=O)CS | COC(=O)c1sc(C(F)(F)F)cc1O | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | 77dd272d651c2798c3c9424a71f8bba3dd13045a7eea6e89b42541b338cbddd5 | cb4d41d978c3d8970a717baa1898aebe45e360b2a07c34662ddbc01c205b9792 | c1ccsc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D2;+0:3]=[C;H0;D3;+0:4](-O-C)-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[SH;D1;+0:14]>>[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:13]1:[s;H0;D2;+0:14]:[c;H0;D3;+0:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1... | 91.2 | [{"value": 91.0, "product": "COC(=O)C=1SC(=CC1O)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "COC(=O)C=1SC(=CC1O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 4,4,4-trifluoro-3-methoxy-but-2-enoic acid ethyl ester (9.6 g, 48.5 mmol) and methyl thioglycolate (4.3 mL, 48.5 mmol) in MeOH (75 mL) is cooled to 5° C. A solution of KOH (3.3 g, 58.2 mmol) in MeOH (75 mL) is then added over 30 min. The reaction mixture is stirred overnight at room temperature. The react... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Aliphatic thiol | Ester.Aromatic alcohol | null | c1ccsc1 | c1ccsc1 | HO- | CO.O | null | 8 | CCOC(=O)C=C(OC)C(F)(F)F.COC(=O)CS>CO.O>COC(=O)c1sc(C(F)(F)F)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-97bd380cae1c4e708eb824535de2f9eb | Clc1nnnn1-c1ccccc1.Oc1csc(C(F)(F)F)c1>>FC(F)(F)c1cc(Oc2nnnn2-c2ccccc2)cs1 | FC(C1=CC(=CS1)O)(F)F.ClC1=NN=NN1C1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+]>>C1(=CC=CC=C1)N1N=NN=C1OC1=CSC(=C1)C(F)(F)F | Cl[c:9]1[n:10][n:11][n:12][n:13]1-[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7]([OH:8])[cH:20][s:21]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[n:10][n:11][n:12][n:13]2-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][s:21]1 | Clc1nnnn1-c1ccccc1.Oc1csc(C(F)(F)F)c1 | FC(F)(F)c1cc(Oc2nnnn2-c2ccccc2)cs1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b0b5fa75f8d32dfc2c1c81f67556be0cd9accee81c6065b457dea599b9ba080f | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(-n2nnnc2Oc2ccsc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[#7;a:4]:[#7;a:5]:1-[c:6].[OH;D1;+0:7]-[c:8]1:[c:9]:[#16;a:10]:[c:11]:[c:12]:1>>[c:6]-[#7;a:5]1:[#7;a:4]:[#7;a:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:7]-[c:8]1:[c:9]:[#16;a:10]:[c:11]:[c:12]:1 | 68 | [{"value": 68.0, "product": "C1(=CC=CC=C1)N1N=NN=C1OC1=CSC(=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "C1(=CC=CC=C1)N1N=NN=C1OC1=CSC(=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-trifluoromethyl-thiophen-3-ol (2.0 g, 11.9 mmol) in dry acetone (480 mL) containing 5-chloro-1-phenyl-1H-tetrazole (2.1 g, 11.9 mmol) and K2CO3 (3.3 g, 23.8 mmol) is maintained at reflux with careful exclusion of moisture overnight. The acetone is removed under reduced pressure and the residue is partit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1nnn[nH]1 | c1nnn[nH]1 | c1ccsc1.c1nnn[nH]1.c1ccccc1 | HCl | CC(=O)C | null | null | Clc1nnnn1-c1ccccc1.Oc1csc(C(F)(F)F)c1>CC(=O)C>FC(F)(F)c1cc(Oc2nnnn2-c2ccccc2)cs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83b360ca114c47f9936ef07085d51598 | NS(=O)(=O)c1ccc(-n2nnnc2Oc2cc(C(F)(F)F)sc2S(N)(=O)=O)cc1>>NS(=O)(=O)c1ccc(C(F)(F)F)s1 | S(N)(=O)(=O)C1=CC=C(C=C1)N1N=NN=C1OC1=C(SC(=C1)C(F)(F)F)S(=O)(=O)N.O.CCO.C(=O)O>>FC(C1=CC=C(S1)S(=O)(=O)N)(F)F | NS(=O)(=O)c1ccc(-n2nnnc2O[c:6]2[c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[s:13][c:8]([C:9]([F:10])([F:11])[F:12])[cH:7]2)cc1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[s:13]1 | NS(=O)(=O)c1ccc(-n2nnnc2Oc2cc(C(F)(F)F)sc2S(N)(=O)=O)cc1 | NS(=O)(=O)c1ccc(C(F)(F)F)s1 | null | [Pd] | C1=CC=CC=C1 | Reduction | OtherReaction | ba5bfc5b3482059af1846468354831d20c4ccc44b6a82b8e0c59a2e82917dd0f | aa7cf63c080af8644a576d884d07cafb9f1b7f6e4bb39c7f680496e99a92bb91 | c1ccsc1 | N-S(=O)(=O)-c1:c:c:c(-n2:n:n:n:c:2-O-[c;H0;D3;+0:1]2:[c:2]:[c:3](-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]):[#16;a:8]:[c:9]:2-[#16:10]):c:c:1>>[#16:10]-[c:9]1:[#16;a:8]:[c:3](-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]):[c:2]:[cH;D2;+0:1]:1 | 17 | [{"value": 17.0, "product": "FC(C1=CC=C(S1)S(=O)(=O)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.6, "product": "FC(C1=CC=C(S1)S(=O)(=O)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 3-[1-(4-sulfamoyl-phenyl)-1H-tetrazol-5-yloxy]-5-trifluoromethyl-thiophene-2-sulfonamide (210 mg, 0.47 mmol) in benzene (50 mL) is added H2O (2 mL), EtOH (3 mL), formic acid (2 mL) and 10% palladium on carbon (350 mg). The mixture is heated to 80° C. overnight. The reaction mixture is cooled to room te... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ether | null | c1ccccc1.c1nnn[nH]1.c1ccsc1 | c1ccsc1 | c1ccsc1 | HO- | [Pd].C1=CC=CC=C1 | 80 | null | NS(=O)(=O)c1ccc(-n2nnnc2Oc2cc(C(F)(F)F)sc2S(N)(=O)=O)cc1>[Pd].C1=CC=CC=C1>NS(=O)(=O)c1ccc(C(F)(F)F)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-084376ff6cbd402bbcddd99c0de3c3d7 | NS(=O)(=O)c1ccc(Br)s1.O=C(O)c1ccc(Br)cc1Cl>>O=C(NS(=O)(=O)c1ccc(Br)s1)c1ccc(Br)cc1Cl | CC=1C=CC(=CC1)S(=O)(=O)O.BrC1=CC=C(S1)S(=O)(=O)N.BrC1=CC(=C(C(=O)O)C=C1)Cl>>BrC1=CC(=C(C(=O)NS(=O)(=O)C=2SC(=CC2)Br)C=C1)Cl | [NH2:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[s:12]1.O[C:2](=[O:1])[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]1[Cl:20]>>[O:1]=[C:2]([NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[s:12]1)[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]1[Cl:20] | NS(=O)(=O)c1ccc(Br)s1.O=C(O)c1ccc(Br)cc1Cl | O=C(NS(=O)(=O)c1ccc(Br)s1)c1ccc(Br)cc1Cl | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1cccs1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#16;a:6]:[c:7]-[#16:8](-[NH2;D1;+0:9])(=[O;D1;H0:10])=[O;D1;H0:11]>>[#16;a:6]:[c:7]-[#16:8](=[O;D1;H0:10])(=[O;D1;H0:11])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 72 | HOUR | An 8 mL reaction vial is charged with 4-bromo-2-chlorobenzoic acid (0.39 mmol, 1.5 eq) and 2.0 mL of dichloromethane. A stock solution (4.0 mL) containing 5-bromothiophene-2-sulfonamide (0.26 mmol, 1 eq) and N,N-[dimethyl]-4-aminopyridine (48 mg, 0.39 mmol, 1.5 eq) in dichloromethane is added, followed by 0.261 g carbo... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccsc1.c1ccccc1 | HO- | ClCCl | null | 72 | NS(=O)(=O)c1ccc(Br)s1.O=C(O)c1ccc(Br)cc1Cl>ClCCl>O=C(NS(=O)(=O)c1ccc(Br)s1)c1ccc(Br)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9cde62dad74542a8b096bc1839d1215f | COCCOCCOCCO.O=C(Cl)C1CC1>>COCCOCCOCCOC(=O)C1CC1 | COCCOCCOCCO.C(C)N(CC)CC.C1(CC1)C(=O)Cl>>C1(CC1)C(=O)OCCOCCOCCOC | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11].Cl[C:12](=[O:13])[CH:14]1[CH2:15][CH2:16]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][C:12](=[O:13])[CH:14]1[CH2:15][CH2:16]1 | COCCOCCOCCO.O=C(Cl)C1CC1 | COCCOCCOCCOC(=O)C1CC1 | null | null | ClCCl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1 | null | [] | 0 | CELSIUS | 1 | HOUR | Triethylene glycol monomethyl ether (1.1 eq, 5.26 mmol, 0.84 ml), triethylamine (1.1 eq, 5.26 mmol, 0.73 ml) was taken in a 10 ml round bottom flask and dichloromethane (3 ml) was added. This mixture was cooled to 0° C. and then cyclopropanecarbonyl chloride (4.78 mmol, 0.5 g, 0.43 ml) was added in a dropwise fashion m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1CC1 | HCl | ClCCl | 0 | 1 | COCCOCCOCCO.O=C(Cl)C1CC1>ClCCl>COCCOCCOCCOC(=O)C1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cdfc09446c49400d80ac411e2e633a6a | CCN(CC)CC.CS(=O)(=O)Cl.OCCc1ccc(O)cc1>>CS(=O)(=O)OCCc1ccc(OS(C)(=O)=O)cc1 | C(C)N(CC)CC.OC1=CC=C(C=C1)CCO.CS(=O)(=O)Cl>>CS(=O)(=O)OCCC1=CC=C(C=C1)OS(=O)(=O)C | CCN(CC)C[CH3:14].Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:17][cH:18]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][S:13]([CH3:14])(=[O:15])=[O:16])[cH:17][cH:18]1 | CCN(CC)CC.CS(=O)(=O)Cl.OCCc1ccc(O)cc1 | CS(=O)(=O)OCCc1ccc(OS(C)(=O)=O)cc1 | null | null | C(Cl)Cl | Oxidation | OtherReaction | c36003d3b803e6ac0bbdc324c0694f01c1c5ae153a9aa61e12ae47160d56be56 | adf4599ac843f34885822a3073d4ca4e8ae92d6092b8cb127254061af10f08be | c1ccccc1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-[S;H0;D4;+0:2](-[C;D1;H3:3])(=[O;D1;H0:4])=[O;D1;H0:5].[C:6]-[C:7]-[OH;D1;+0:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[CH3;D1;+0:1]-[#16:13](=[O;D1;H0:14])(=[O;D1;H0:15])-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12].[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:2](-[C;D1;H3:3])(=[O;D1;H0:4])=[O;D1;H0:5] | null | [] | -20 | CELSIUS | null | null | 2-(4-Hydroxyphenyl)ethanol(356 g, 2.58 mol, 1.0 eq) was dissolved in methylene chloride (3500 ml) and triethyl amine (653 g, 6.44 mol, 2.5 eq). The mixture was cooled to −20° C. Methanesulfonyl chloride (657 g, 5.74 mol. 2.2 eq) was then added keeping the temperature between −25° C. and −15° C. When the conversion was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol.Tertiary amine.Sulfonyl halide | Mesylate.Mesylate | null | null | c1ccccc1 | HCl | C(Cl)Cl | -20 | null | CCN(CC)CC.CS(=O)(=O)Cl.OCCc1ccc(O)cc1>C(Cl)Cl>CS(=O)(=O)OCCc1ccc(OS(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc6cc8363cff42a4af4528dcc64a7236 | CCOC(=O)[C@H](Cc1ccc(OCCc2ccc(OS(C)(=O)=O)cc2)cc1)OCC>>CCO[C@@H](Cc1ccc(OCCc2ccc(OS(C)(=O)=O)cc2)cc1)C(=O)O | [OH-].[Li+].C(C)O[C@H](C(=O)OCC)CC1=CC=C(C=C1)OCCC1=CC=C(C=C1)OS(=O)(=O)C.O1CCCC1.O>>C(C)O[C@H](C(=O)O)CC1=CC=C(C=C1)OCCC1=CC=C(C=C1)OS(=O)(=O)C | CC[O:28][C:26]([C@@H:4]([O:3][CH2:2][CH3:1])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][cH:23]2)[cH:24][cH:25]1)=[O:27]>>[CH3:1][CH2:2][O:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17]... | CCOC(=O)[C@H](Cc1ccc(OCCc2ccc(OS(C)(=O)=O)cc2)cc1)OCC | CCO[C@@H](Cc1ccc(OCCc2ccc(OS(C)(=O)=O)cc2)cc1)C(=O)O | null | null | C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CCOc2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 30 | MINUTE | To the oil of ethyl (S)-2-ethoxy-3-[4-[[4-(methylsulfonyloxy)phenethyl]oxy]phenyl]propanoate (723 g(71.2% assay), 1.18 mol, 1.0 eq) was added tetrahydrofuran (THF) (3900 ml). When a homogenous solution was formed, water (900 ml) was added. The mixture was cooled to +10° C. Lithium hydroxide solution (390 ml, 4 M, 1.45 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC | null | 0.5 | CCOC(=O)[C@H](Cc1ccc(OCCc2ccc(OS(C)(=O)=O)cc2)cc1)OCC>C(C)(=O)OCC>CCO[C@@H](Cc1ccc(OCCc2ccc(OS(C)(=O)=O)cc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fbb70cf1aa6d4f91b0623384d82a6ec4 | BrBr.O=C1Cc2ccccc2N1>>O=C1Cc2cc(Br)ccc2N1 | O.N1C(CC2=CC=CC=C12)=O.C(C)(=O)[O-].[Na+].BrBr>>BrC=1C=C2CC(NC2=CC1)=O | Br[Br:7].[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][cH:6][cH:8][cH:9][c:10]2[NH:11]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([Br:7])[cH:8][cH:9][c:10]2[NH:11]1 | BrBr.O=C1Cc2ccccc2N1 | O=C1Cc2cc(Br)ccc2N1 | null | null | CCOC(=O)C.C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | e5aad40fc3ec640bed45a7119ff569558b20c39979304f365dafdbc5ae4e4cd4 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Cc2ccccc2N1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 97.3 | [{"value": 96.0, "product": "BrC=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "BrC=1C=C2CC(NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueo... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HBr | CCOC(=O)C.C(Cl)(Cl)Cl | null | 0.5 | BrBr.O=C1Cc2ccccc2N1>CCOC(=O)C.C(Cl)(Cl)Cl>O=C1Cc2cc(Br)ccc2N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-73b578707101440ab23e494441247e5a | O=C1Cc2cc(Br)ccc2N1.O=[N+]([O-])c1cccc(B(O)O)c1>>O=C1Cc2cc(-c3cccc([N+](=O)[O-])c3)ccc2N1 | BrC=1C=C2CC(NC2=CC1)=O.[N+](=O)([O-])C=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>[N+](=O)([O-])C=1C=C(C=CC1)C=1C=C2CC(NC2=CC1)=O | Br[c:6]1[cH:5][c:4]2[c:18]([cH:17][cH:16]1)[NH:19][C:2](=[O:1])[CH2:3]2.OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]3)[cH:16][cH:17][c:18]2[NH:19]1 | O=C1Cc2cc(Br)ccc2N1.O=[N+]([O-])c1cccc(B(O)O)c1 | O=C1Cc2cc(-c3cccc([N+](=O)[O-])c3)ccc2N1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 65 | [{"value": 65.0, "product": "[N+](=O)([O-])C=1C=C(C=CC1)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.5, "product": "[N+](=O)([O-])C=1C=C(C=CC1)C=1C=C2CC(NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-bromo-2-indolinone (1.08 g, 5.09 mmol) and tetrakistriphenyl phosphine Pd (0) (0.273 g) were stirred under an atmosphere of nitrogen in ethylene glycol dimethyl ether (35 mL). After 15 minutes, 3-nitrophenyl boronic acid (1.70 g, 10.2 mmol) was added, followed by potassium carbonate (4.24 g, 30.7 mmol) in water (15 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.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.COCCOC | null | 0.25 | O=C1Cc2cc(Br)ccc2N1.O=[N+]([O-])c1cccc(B(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>O=C1Cc2cc(-c3cccc([N+](=O)[O-])c3)ccc2N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30b90ddcbdb4472aae87c4606838feb4 | BrBr.CC1C(=O)Nc2ccccc21>>CC1=c2cc(Br)ccc2=NC1=O | C([O-])([O-])=O.[Na+].[Na+].BrBr.CC1C(NC2=CC=CC=C12)=O.C(C)(=O)[O-].[Na+]>>BrC1=CC2=C(C(N=C2C=C1)=O)C | Br[Br:6].[CH3:1][CH:2]1[c:3]2[cH:4][cH:5][cH:7][cH:8][c:9]2[NH:10][C:11]1=[O:12]>>[CH3:1][C:2]1=[c:3]2[cH:4][c:5]([Br:6])[cH:7][cH:8][c:9]2=[N:10][C:11]1=[O:12] | BrBr.CC1C(=O)Nc2ccccc21 | CC1=c2cc(Br)ccc2=NC1=O | null | null | C(C)(=O)O | Functional Group Interconversion | OtherReaction | f77276f67562534d698ae9969b38604bf6d0631d673dbcf49471739b8fb2dc9c | 10d5e9f7ea4e0a6d7c64f3eede8b2722c836d0e851a0ab7fb8f5aa5d2bdff633 | O=C1C=c2ccccc2=N1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[CH;D3;+0:3]1-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c;H0;D3;+0:7]2:[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c;H0;D3;+0:12]:2-1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:10]1:[c:11]:[c;H0;D3;+0:12]2:[c;H0;D3;+0:7](:[c:8]:[c:9]:1)=[N;H0;D2;+0:6]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:3]=2-[C;D1;H3:2] | 93.7 | [{"value": 93.0, "product": "BrC1=CC2=C(C(N=C2C=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "BrC1=CC2=C(C(N=C2C=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | Under an atmosphere of nitrogen, bromine (0.96 g, 6.0 mmol) in acetic acid (5 cm3) was added drop wise to a solution of 3-methyl-2-indolinone (0.8749 g, 6.0 mmol) (Kende, et al, Synth. Commun., 12, 1, 1982) and sodium acetate (0.50 g, 6.0 mmol) in acetic acid (10 cm3). The reaction was stirred at room temperature for 3... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Aromatic halide | c1ccc2c(c1)CCN2 | C1=c2ccccc2=NC1 | C1=c2ccccc2=NC1 | HBr | C(C)(=O)O | null | 3.5 | BrBr.CC1C(=O)Nc2ccccc21>C(C)(=O)O>CC1=c2cc(Br)ccc2=NC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f1ad471805684fc5b6ebc2d669085dc4 | CC1C(=O)Nc2ccc(Br)cc21>>CC1=c2cc(Br)ccc2=NC1=O | [Cl-].[NH4+].BrC=1C=C2C(C(NC2=CC1)=O)C.[N+](=O)([O-])C=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>BrC1=CC2=C(C(N=C2C=C1)=O)C | [CH3:1][CH:2]1[c:3]2[cH:4][c:5]([Br:6])[cH:7][cH:8][c:9]2[NH:10][C:11]1=[O:12]>>[CH3:1][C:2]1=[c:3]2[cH:4][c:5]([Br:6])[cH:7][cH:8][c:9]2=[N:10][C:11]1=[O:12] | CC1C(=O)Nc2ccc(Br)cc21 | CC1=c2cc(Br)ccc2=NC1=O | 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(OC)COC | Oxidation | OtherReaction | 5888764ac5705b4fccbaa0f333db96bf6faba4a5ea8e8011bddc2ecf15e91da3 | 951ba0a3ea11fb59b51e8c5a89ac77de7d3f3bdc1496c8df7b8fa4f398d1bd93 | O=C1C=c2ccccc2=N1 | [C;D1;H3:1]-[CH;D3;+0:2]1-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2-1>>[C;D1;H3:1]-[C;H0;D3;+0:2]1=[c;H0;D3;+0:11]2:[c:10]:[c:9]:[c:8]:[c:7]:[c;H0;D3;+0:6]:2=[N;H0;D2;+0:5]-[C:3]-1=[O;D1;H0:4] | 60.3 | [{"value": 47.0, "product": "BrC1=CC2=C(C(N=C2C=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.3, "product": "BrC1=CC2=C(C(N=C2C=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-Bromo-3-methyl-1,3-dihydro-indol-2-one (0.50 g, 2.22 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.15 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (18 cm3). After 15 min., 3-nitrophenyl boronic acid (0.74 g, 4.45 mmol) was added, followed by potassium carbonate (1.86 g, 13.5 mmol) in wat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)CCN2 | C1=c2ccccc2=NC1 | C1=c2ccccc2=NC1 | 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(OC)COC | null | 0.25 | CC1C(=O)Nc2ccc(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(OC)COC>CC1=c2cc(Br)ccc2=NC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-78f0cb74792a4655a3abe774e955057c | CC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>>CC1(C)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | BrC=1C=C2C(C(NC2=CC1)=O)(C)C.ClC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)C | Br[c:10]1[cH:9][cH:8][c:7]2[c:19]([cH:18]1)[C:2]([CH3:1])([CH3:3])[C:4](=[O:5])[NH:6]2.OB(O)[c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]1>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]3)[cH:18][c:19]21 | CC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1 | CC1(C)C(=O)Nc2ccc(-c3cccc(Cl)c3)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(OC)COC.[Cl-].[NH4+] | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 25 | [{"value": 25.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (0.98 g, 4.07 mol) and, tetrakis(triphenylphosphine)palladium(0) (0.239 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (35 cm3). After 15 min., 3-chlorophenylboronic acid (1.27 g, 8.13 mol) was added, followed by potassium carbonate (3.40 g, 45 mmol) i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.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(OC)COC.[Cl-].[NH4+] | null | 0.25 | CC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC.[Cl-].[NH4+]>CC1(C)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31d1fe9f37be4dd1a460278d3b248409 | CC1(C)C(=O)Nc2ccc(Br)cc21.O=[N+]([O-])c1cccc(B(O)O)c1>>CC1(C)C(=O)Nc2ccc(-c3cccc([N+](=O)[O-])c3)cc21 | [Cl-].[NH4+].BrC=1C=C2C(C(NC2=CC1)=O)(C)C.[N+](=O)([O-])C=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>CC1(C(NC2=CC=C(C=C12)C1=CC(=CC=C1)[N+](=O)[O-])=O)C | Br[c:10]1[cH:9][cH:8][c:7]2[c:21]([cH:20]1)[C:2]([CH3:1])([CH3:3])[C:4](=[O:5])[NH:6]2.OB(O)[c:11]1[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]1>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]3)[cH:20][c:21]21 | CC1(C)C(=O)Nc2ccc(Br)cc21.O=[N+]([O-])c1cccc(B(O)O)c1 | CC1(C)C(=O)Nc2ccc(-c3cccc([N+](=O)[O-])c3)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 | CCOC(=O)C.O.C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 119 | [{"value": 67.0, "product": "CC1(C(NC2=CC=C(C=C12)C1=CC(=CC=C1)[N+](=O)[O-])=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 119.0, "product": "CC1(C(NC2=CC=C(C=C12)C1=CC(=CC=C1)[N+](=O)[O-])=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (1.02 g, 4.26 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.244 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (35 cm3). After 15 minutes, 3-nitrophenylboronic acid (1.43 g, 2.56 mmol) was added, followed by potassium carbonate (3.54 g, 2.56 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.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.CCOC(=O)C.O.C(OC)COC | null | 0.25 | CC1(C)C(=O)Nc2ccc(Br)cc21.O=[N+]([O-])c1cccc(B(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCOC(=O)C.O.C(OC)COC>CC1(C)C(=O)Nc2ccc(-c3cccc([N+](=O)[O-])c3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ed7f37270af420fb0e5d51ef1f37326 | CCI.O=C1Cc2ccccc2N1>>CCC1=c2ccccc2=NC1=O | ICC.N1C(CC2=CC=CC=C12)=O.C(CCC)[Li].[NH4+].[Cl-].CN(CCN(C)C)C>>C(C)C=1C(N=C2C=CC=CC12)=O | I[CH2:2][CH3:1].[CH2:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[NH:10][C:11]1=[O:12]>>[CH3:1][CH2:2][C:3]1=[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2=[N:10][C:11]1=[O:12] | CCI.O=C1Cc2ccccc2N1 | CCC1=c2ccccc2=NC1=O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 7f8efd166912a03506850ad77dd8b310e9bbf110f40dc0aa3466aad53303d70b | 9795126e672adf3dfeb9ebcd165d02e10eb1b4ac31d83997fdca7c7a739d39dc | O=C1C=c2ccccc2=N1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[C:4]1-[CH2;D2;+0:5]-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2-[NH;D2;+0:12]-1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:5]1=[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2=[N;H0;D2;+0:12]-[C:4]-1=[O;D1;H0:3] | 2.9 | [{"value": 2.9, "product": "C(C)C=1C(N=C2C=CC=CC12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of oxindole (40 g, 0.3 mol) in dry THF (400 ml) under N2 was cooled to −25° C. and treated drop wise with n-butyl lithium (2.5M in hexanes, 240 ml, 0.6 mol). To the resulting solution was added N,N,N′,N′-tetramethylethylenediamine (90.4 ml, 0.6 mol). After 30 min. iodoethane (48 ml, 0.6 mol) was added and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | null | c1ccc2c(c1)CCN2 | C1=c2ccccc2=NC1 | C1=c2ccccc2=NC1 | HI | C1CCOC1 | null | null | CCI.O=C1Cc2ccccc2N1>C1CCOC1>CCC1=c2ccccc2=NC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7d68ef0a88f48f89e4a0c15da7d1571 | BrBr.CCC1C(=O)Nc2ccccc21>>CCC1C(=O)Nc2ccc(Br)cc21 | C(C)C1C(NC2=CC=CC=C12)=O.C(C)(=O)[O-].[Na+].BrBr>>BrC=1C=C2C(C(NC2=CC1)=O)CC | Br[Br:11].[CH3:1][CH2:2][CH:3]1[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][cH:10][cH:12][c:13]21>>[CH3:1][CH2:2][CH:3]1[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]21 | BrBr.CCC1C(=O)Nc2ccccc21 | CCC1C(=O)Nc2ccc(Br)cc21 | null | null | O.C(C)(=O)O | Functional Group Interconversion | Bromination | e5aad40fc3ec640bed45a7119ff569558b20c39979304f365dafdbc5ae4e4cd4 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Cc2ccccc2N1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | null | [] | null | null | null | null | A solution of 3-ethyloxindole (6.0 g, 40 mmol) and sodium acetate (4 g, 48 mmol) in acetic acid (100 ml) was treated with bromine (6.4 g, 40 mmol). After 30 min. the mixture was diluted with water and extracted with EtOAc (2×); the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution,... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HBr | O.C(C)(=O)O | null | null | BrBr.CCC1C(=O)Nc2ccccc21>O.C(C)(=O)O>CCC1C(=O)Nc2ccc(Br)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-099a937005364924bd6eae4d9b0b8422 | BrBr.CCC1(CC)C(=O)Nc2ccccc21>>CCC1(CC)C(=O)Nc2ccc(Br)cc21 | C(C)C1(C(NC2=CC=CC=C12)=O)CC.C(C)(=O)[O-].[Na+].BrBr>>BrC=1C=C2C(C(NC2=CC1)=O)(CC)CC | Br[Br:13].[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:14][c:15]21>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]21 | BrBr.CCC1(CC)C(=O)Nc2ccccc21 | CCC1(CC)C(=O)Nc2ccc(Br)cc21 | null | null | O.C(C)(=O)O | Functional Group Interconversion | Bromination | e5aad40fc3ec640bed45a7119ff569558b20c39979304f365dafdbc5ae4e4cd4 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Cc2ccccc2N1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | null | [] | null | null | null | null | A solution of 3,3-diethylindol-2-one (8 g, 40 mmol) and sodium acetate (4 g, 48 mmol) in acetic acid (100 ml) was treated with bromine (6.4 g, 40 mmol). After 30 min. the mixture was diluted with water and extracted with EtOAc (2×); the combined organic layers were washed with water, sat. sodium hydrogen carbonate solu... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HBr | O.C(C)(=O)O | null | null | BrBr.CCC1(CC)C(=O)Nc2ccccc21>O.C(C)(=O)O>CCC1(CC)C(=O)Nc2ccc(Br)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-685d956059c54290a7022e11e3dec19f | O=C1Nc2ccc(Br)cc2C1=O>>CC1(O)C(=O)Nc2ccc(Br)cc21 | BrC=1C=C2C(C(NC2=CC1)=O)=O.C[Mg]Br.[Cl-].[NH4+]>>BrC=1C=C2C(C(NC2=CC1)=O)(C)O | [C:2]1(=[O:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]21>>[CH3:1][C:2]1([OH:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]21 | O=C1Nc2ccc(Br)cc2C1=O | CC1(O)C(=O)Nc2ccc(Br)cc21 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | e206534f58e7b072db5c84f71beb0f8b81df4661d962843e524e4fc82e2a18c5 | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | O=C1Cc2ccccc2N1 | [O;D1;H0:1]=[C:2]1-[#7:3]-[c:4]:[c:5](:[c:6])-[C;H0;D3;+0:7]-1=[O;H0;D1;+0:8]>>[C;D1;H3:9]-[C;H0;D4;+0:7]1(-[OH;D1;+0:8])-[C:2](=[O;D1;H0:1])-[#7:3]-[c:4]:[c:5]-1:[c:6] | 29 | [{"value": 29.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)(C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.7, "product": "BrC=1C=C2C(C(NC2=CC1)=O)(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-bromoisatin (5.0 g, 22 mmol) in dry THF (50 cm3) under N2 was cooled to 0° C. and treated drop-wise with methyl magnesium bromide (3M in diethylether, 14.7 cm3, 44 mmol) and the mixture was allowed to warm up-to room temperature. The reaction was poured into sat. ammonium chloride solution, then extract... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | C1CCOC1 | null | null | O=C1Nc2ccc(Br)cc2C1=O>C1CCOC1>CC1(O)C(=O)Nc2ccc(Br)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a4bc0c246c5c49f69c45dc9f684b7b07 | CC1(O)C(=O)Nc2ccc(Br)cc21.COS(=O)(=O)c1ccc(C)cc1>>COC1(C)C(=O)Nc2ccc(Br)cc21 | [Cl-].[NH4+].CC(C)([O-])C.[K+].BrC=1C=C2C(C(NC2=CC1)=O)(C)O.COS(=O)(=O)C1=CC=C(C=C1)C>>BrC=1C=C2C(C(NC2=CC1)=O)(C)OC | [OH:2][C:3]1([CH3:4])[C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]21.Cc1ccc(S(=O)(=O)O[CH3:1])cc1>>[CH3:1][O:2][C:3]1([CH3:4])[C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]21 | CC1(O)C(=O)Nc2ccc(Br)cc21.COS(=O)(=O)c1ccc(C)cc1 | COC1(C)C(=O)Nc2ccc(Br)cc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | O-methylation | 6e2efd44e881e9405bbc2be63bf815d40117fbb9fa6dc2effac725e566998d9a | 81d2e2c5cd7c0d967284864f20b2202e3b06dde03416092c701808131566c9f8 | O=C1Cc2ccccc2N1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH3;D1;+0:1]):c:c:1.[C;D1;H3:2]-[C:3]1(-[OH;D1;+0:4])-[c:5]:[c:6]-[#7:7]-[C:8]-1=[O;D1;H0:9]>>[C;D1;H3:2]-[C:3]1(-[O;H0;D2;+0:4]-[CH3;D1;+0:1])-[c:5]:[c:6]-[#7:7]-[C:8]-1=[O;D1;H0:9] | 53.7 | [{"value": 53.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)(C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.7, "product": "BrC=1C=C2C(C(NC2=CC1)=O)(C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 5-bromo-3-hydroxy-3-methyl-1,3-dihydro-indol-2-one (1.0 g, 4.1 mmol) was dissolved in dry DMF (15 cm3) cooled to 0° C. and treated with potassium tert-butoxide (1M in THF, 4.5 cm3, 4.5 mmol). After 15 min. methyl-p-toluenesulfonate (0.93 g, 5 mmol) was added and the mixture was allowed to warm up-to room temperature. A... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Tertiary alcohol | Ether | c1ccccc1 | null | c1ccc2c(c1)CCN2 | TsOH.HO- | CN(C)C=O | 0 | null | CC1(O)C(=O)Nc2ccc(Br)cc21.COS(=O)(=O)c1ccc(C)cc1>CN(C)C=O>COC1(C)C(=O)Nc2ccc(Br)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae65edd3a66e4dce8e06b975bf92e269 | COC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>>COC1(C)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | ClC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].BrC=1C=C2C(C(NC2=CC1)=O)(C)OC>>ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)OC | Br[c:11]1[cH:10][cH:9][c:8]2[c:20]([cH:19]1)[C:3]([O:2][CH3:1])([CH3:4])[C:5](=[O:6])[NH:7]2.OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]1>>[CH3:1][O:2][C:3]1([CH3:4])[C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]3)[cH:19][c:20]21 | COC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1 | COC1(C)C(=O)Nc2ccc(-c3cccc(Cl)c3)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(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 29 | [{"value": 29.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 5-bromo-3-methoxy-3-methyl-1,3-dihydro-indol-2-one (0.52 g, 2.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) was dissolved in dimethoxyethane (22 cm3). After 15 min., 3-chlorophenylboronic acid (0.63 g, 4.1 mmol) and sodium carbonate (1.0 g) in water (10 cm3) was added and the rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.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(OC)COC | null | 0.25 | COC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC>COC1(C)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-11c8f6a6d49c4e53ba77cc33793f0bd3 | CC#[C][Mg][Br].O=C1Nc2ccc(Br)cc2C1=O>>CC#CC1(O)C(=O)Nc2ccc(Br)cc21 | [Cl-].[NH4+].BrC=1C=C2C(C(NC2=CC1)=O)=O.C(#CC)[Mg]Br>>BrC=1C=C2C(C(NC2=CC1)=O)(C#CC)O | [Br][Mg][C:3]#[C:2][CH3:1].[C:4]1(=[O:5])[C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]21>>[CH3:1][C:2]#[C:3][C:4]1([OH:5])[C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]21 | CC#[C][Mg][Br].O=C1Nc2ccc(Br)cc2C1=O | CC#CC1(O)C(=O)Nc2ccc(Br)cc21 | null | null | C1CCOC1 | C-C Coupling | Grignard from ketone to alcohol | 047bdb50f80bc54c741bf0904b2597c43eb1b755af59b6d94feb30812db22dae | 14e780921369c95ed40af45076e892db051e7adf9725dbd330196dcdac285701 | O=C1Cc2ccccc2N1 | [Br]-[Mg]-[C;H0;D2;+0:1]#[C:2]-[C;D1;H3:3].[O;D1;H0:4]=[C:5]1-[#7:6]-[c:7]:[c:8](:[c:9])-[C;H0;D3;+0:10]-1=[O;H0;D1;+0:11]>>[C;D1;H3:3]-[C:2]#[C;H0;D2;+0:1]-[C;H0;D4;+0:10]1(-[OH;D1;+0:11])-[C:5](=[O;D1;H0:4])-[#7:6]-[c:7]:[c:8]-1:[c:9] | 97 | [{"value": 97.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)(C#CC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.4, "product": "BrC=1C=C2C(C(NC2=CC1)=O)(C#CC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-bromoisatin (2.5 g, 11 mmol) in dry THF (100 cm3) at −10° C. under a nitrogen atmosphere was added 1-propynylmagnesium bromide (0.5 M in THF, 47 cm3, 23.5 mmol). After 1 h, the mixture was poured into saturated ammonium chloride and extracted with EtOAc (×3), washed with brine, dried (MgSO4) and evap... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone.Alkyne | Tertiary alcohol.Alkyne | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Br-.Mg | C1CCOC1 | null | 1 | CC#[C][Mg][Br].O=C1Nc2ccc(Br)cc2C1=O>C1CCOC1>CC#CC1(O)C(=O)Nc2ccc(Br)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26adb8c2c647457e80fdfa7a30ae1c31 | CC#CC1(OC)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>>CC#CC1(OC)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | ClC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].BrC=1C=C2C(C(NC2=CC1)=O)(C#CC)OC>>ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C#CC)OC | Br[c:13]1[cH:12][cH:11][c:10]2[c:22]([cH:21]1)[C:4]([C:3]#[C:2][CH3:1])([O:5][CH3:6])[C:7](=[O:8])[NH:9]2.OB(O)[c:14]1[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]1>>[CH3:1][C:2]#[C:3][C:4]1([O:5][CH3:6])[C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]3)[cH:21][c:22]21 | CC#CC1(OC)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1 | CC#CC1(OC)C(=O)Nc2ccc(-c3cccc(Cl)c3)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(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 15 | [{"value": 15.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C#CC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)(C#CC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-bromo-3-methoxy-3-prop-1-ynyl-1,3-dihydroindol-2-one (0.56 g, 2.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.10 mmol) were stirred at room temperature in dimethoxyethane (22 cm3). After 15 min. 3-chlorophenylboronic acid (0.63 g, 4.0 mmol) and sodium carbonate (1.06 g, 10 mmol) in water (11 cm3) we... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.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(OC)COC | null | 0.25 | CC#CC1(OC)C(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC>CC#CC1(OC)C(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c09160befb0a446b9eccd6a4f009836e | O=C1Cc2cc(Br)ccc2N1.OB(O)c1cccc(Cl)c1>>O=C1Cc2cc(-c3cccc(Cl)c3)ccc2N1 | BrC=1C=C2CC(NC2=CC1)=O.ClC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>ClC=1C=C(C=CC1)C=1C=C2CC(NC2=CC1)=O | Br[c:6]1[cH:5][c:4]2[c:16]([cH:15][cH:14]1)[NH:17][C:2](=[O:1])[CH2:3]2.OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]3)[cH:14][cH:15][c:16]2[NH:17]1 | O=C1Cc2cc(Br)ccc2N1.OB(O)c1cccc(Cl)c1 | O=C1Cc2cc(-c3cccc(Cl)c3)ccc2N1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O.C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 86 | [{"value": 86.0, "product": "ClC=1C=C(C=CC1)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.3, "product": "ClC=1C=C(C=CC1)C=1C=C2CC(NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the 5-bromoxindole (0.5 g, 2.4 mmol) and tetrakis(triphenylphosphine) palladium (0.14 g, 0.12 mmol) in dimethoxyethane (10 cm3) was stirred under N2 for 20 min. To this mixture was then added 3-chlorophenylboronic acid (0.44 g, 2.83 mmol) and sodium carbonate (0.75 g, 7.1 mmol) in water (4 cm3). The solut... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.C(OC)COC | null | null | O=C1Cc2cc(Br)ccc2N1.OB(O)c1cccc(Cl)c1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.C(OC)COC>O=C1Cc2cc(-c3cccc(Cl)c3)ccc2N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb6667c882384f968c20f1307ce31ead | O=C1Cc2cc(-c3cccc(Cl)c3)ccc2N1>>O=C1Nc2ccc(-c3cccc(Cl)c3)cc2C1=O | ClC=1C=C(C=CC1)C=1C=C2CC(NC2=CC1)=O.O1CCOCC1>>ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)=O | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]3)[cH:15][c:16]2[CH2:17]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12]([Cl:13])[cH:14]3)[cH:15][c:16]2[C:17]1=[O:18] | O=C1Cc2cc(-c3cccc(Cl)c3)ccc2N1 | O=C1Nc2ccc(-c3cccc(Cl)c3)cc2C1=O | null | null | null | Oxidation | OtherReaction | 5c42bc08649ad444bd707dcd6481bf7bab42c2368ef82c0ac85a3860aab46162 | 77bee5a21cba7564f2a068b8a8fb160e4513dc5cbafb6b06748cb7a2efc1051b | O=C1Nc2ccc(-c3ccccc3)cc2C1=O | [O;D1;H0:1]=[C:2]1-[#7:3]-[c:4]:[c:5](:[c:6])-[CH2;D2;+0:7]-1>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[C:2](=[O;D1;H0:1])-[#7:3]-[c:4]:[c:5]-1:[c:6] | 76 | [{"value": 76.0, "product": "ClC=1C=C(C=CC1)C=1C=C2C(C(NC2=CC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-(3-Chloro-phenyl)-1,3-dihydro-indol-2-one (10.0 g, 41 mmol) in dioxane (200 cm3) and SeO2 (22.8 g, 205 mmol) was brought to reflux for 2 h then cooled to RT and concentrated onto Florisil. The Florisil was washed (acetone:CHCl3 1:9) and the combined organic extracts were evaporated. The residue was puri... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1 | Other | null | null | null | O=C1Cc2cc(-c3cccc(Cl)c3)ccc2N1>>O=C1Nc2ccc(-c3cccc(Cl)c3)cc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0951505fdd3d4c26a4e8069af7835193 | ICCCCI.O=C1Cc2ccccc2N1>>O=C1Nc2ccccc2C12CCCC2 | N1C(CC2=CC=CC=C12)=O.C(CCC)[Li].ICCCCI.CN(CCN(C)C)C>>N1C(C2(C3=CC=CC=C13)CCCC2)=O | I[CH2:11][CH2:12][CH2:13][CH2:14]I.[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]12[CH2:11][CH2:12][CH2:13][CH2:14]2 | ICCCCI.O=C1Cc2ccccc2N1 | O=C1Nc2ccccc2C12CCCC2 | null | null | C1CCOC1.O | C-C Coupling | OtherReaction | da305b19e438cec6dd9ecd353ca3cd934886dd4c5b3846022dac2a623fceb79e | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | O=C1Nc2ccccc2C12CCCC2 | I-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-I.[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[C;H0;D4;+0:11]-12-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-2 | 50 | [{"value": 50.0, "product": "N1C(C2(C3=CC=CC=C13)CCCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "N1C(C2(C3=CC=CC=C13)CCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a −25° C. solution of oxindole (2.0 g, 15.0 mmol) in 40 (cm3) of anhydrous THF under N2 was added n-butyllithium (1.6 M in hexanes, 19.7 cm3, 31.5 mmol) drop-wise. To the resulting milky solution was added N,N,N′,N′-tetramethylethylenediamine (4.75 cm3, 31.5 mmol). After 30 min. a solution of 1,4-diiodobutane (21.9 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)NCC21CCCC1 | c1ccc2c(c1)NCC21CCCC1 | HI | C1CCOC1.O | null | 14 | ICCCCI.O=C1Cc2ccccc2N1>C1CCOC1.O>O=C1Nc2ccccc2C12CCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5f70c65da144f20b845befc93cdc22b | BrBr.O=C1Nc2ccccc2C12CCCC2>>O=C1Nc2ccccc2C12CCCC2Br | C(O)([O-])=O.[Na+].N1C(C2(C3=CC=CC=C13)CCCC2)=O.C(C)(=O)[O-].[Na+].BrBr>>BrC1CCCC12C(NC1=CC=CC=C21)=O | Br[Br:15].[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]12[CH2:11][CH2:12][CH2:13][CH2:14]2>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]12[CH2:11][CH2:12][CH2:13][CH:14]2[Br:15] | BrBr.O=C1Nc2ccccc2C12CCCC2 | O=C1Nc2ccccc2C12CCCC2Br | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 5d1ae453742bff017caef24079c4e11e210e4fe7fcd315c0a1d757dce473ae36 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | O=C1Nc2ccccc2C12CCCC2 | Br-[Br;H0;D1;+0:1].[O;D1;H0:2]=[C:3]1-[#7:4]-[c:5]:[c:6]-[C:7]-12-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-2>>[Br;H0;D1;+0:1]-[CH;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:7]-12-[c:6]:[c:5]-[#7:4]-[C:3]-2=[O;D1;H0:2] | 105 | [{"value": 96.0, "product": "BrC1CCCC12C(NC1=CC=CC=C21)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 105.0, "product": "BrC1CCCC12C(NC1=CC=CC=C21)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (0.27 g, 1.4 mmol) and sodium acetate (0.12 g, 1.46 mmol) in acetic acid (10 cm3) was treated with bromine (0.24 g, 1.51 mmol) in acetic acid (2 cm3). After 30 min. the mixture was poured into sat. sodium hydrogen carbonate solution and extracted with EtOAc (... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | c1ccc2c(c1)NCC21CCCC1 | c1ccc2c(c1)NCC21CCCC1 | c1ccc2c(c1)NCC21CCCC1 | HBr | C(C)(=O)O | null | null | BrBr.O=C1Nc2ccccc2C12CCCC2>C(C)(=O)O>O=C1Nc2ccccc2C12CCCC2Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d24153be9c474bb28c86121b580a0c0d | ICCCCCI.O=C1Cc2ccccc2N1>>O=C1Nc2ccccc2C12CCCCC2 | ICCCCCI.N1C(CC2=CC=CC=C12)=O.C(CCC)[Li].[Cl-].[NH4+].CN(CCN(C)C)C>>N1C(C2(C3=CC=CC=C13)CCCCC2)=O | I[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]I.[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]12[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2 | ICCCCCI.O=C1Cc2ccccc2N1 | O=C1Nc2ccccc2C12CCCCC2 | null | null | CCOC(=O)C.O1CCCC1 | C-C Coupling | OtherReaction | 579f0f36d3c1f227acfe012179441842108aef707a45bbf7908129260433618c | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | O=C1Nc2ccccc2C12CCCCC2 | I-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-I.[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D4;+0:12]-12-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-2 | 69.6 | [{"value": 69.6, "product": "N1C(C2(C3=CC=CC=C13)CCCCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.8, "product": "N1C(C2(C3=CC=CC=C13)CCCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of oxindole (25 g, 0.19 mol) in anhydrous tetrahydrofuran (800 cm3) was cooled to −20° C., then n-butyllithium (2.5M in hexanes, 152 cm3, 0.38 mol) was added slowly followed by N,N,N′,N′-tetramethylethylenediamine (51 cm3, 0.38 mol,). After 15 min. 1,5-diiodopentane (174 g, 0.54 mol) was added slowly and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)NCC21CCCCC1 | c1ccc2c(c1)NCC21CCCCC1 | HI | CCOC(=O)C.O1CCCC1 | null | 0.25 | ICCCCCI.O=C1Cc2ccccc2N1>CCOC(=O)C.O1CCCC1>O=C1Nc2ccccc2C12CCCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e265dcbe7a30486b9c3ee7c9ec1cbc9e | BrBr.O=C1Nc2ccccc2C12CCCCC2>>O=C1Nc2ccc(Br)cc2C12CCCCC2 | N1C(C2(C3=CC=CC=C13)CCCCC2)=O.C(C)(=O)[O-].[Na+].BrBr>>BrC=1C=C2C3(C(NC2=CC1)=O)CCCCC3 | Br[Br:8].[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:9][c:10]2[C:11]12[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[C:11]12[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2 | BrBr.O=C1Nc2ccccc2C12CCCCC2 | O=C1Nc2ccc(Br)cc2C12CCCCC2 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | b75a0cb1be6e87ac5ae2a0c4fc61b176231cdf76c6a5c5e00ef053906cd4efba | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Nc2ccccc2C12CCCCC2 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:3]:[c:2] | 67 | [{"value": 67.0, "product": "BrC=1C=C2C3(C(NC2=CC1)=O)CCCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "BrC=1C=C2C3(C(NC2=CC1)=O)CCCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one (17.6 g, 0.09 mol) in acetic acid (300 cm3) was added sodium acetate (8.0 g, 0.1 mol) and bromine (14.6 g, 0.091 mol) with stirring. After 30 min. at room temperature, the reaction mixture was partitioned between water and EtOAc. The aqueous phase was extra... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)NCC21CCCCC1 | c1ccc2c(c1)NCC21CCCCC1 | c1ccc2c(c1)NCC21CCCCC1 | HBr | C(C)(=O)O | null | 0.5 | BrBr.O=C1Nc2ccccc2C12CCCCC2>C(C)(=O)O>O=C1Nc2ccc(Br)cc2C12CCCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da0442915f5d4115aac6c6d518dc2906 | CC(C)(C)OC(=O)n1cccc1B(O)O.O=C1Nc2ccc(Br)cc2C12CCCCC2>>CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 | B(O)(O)C=1N(C=CC1)C(=O)OC(C)(C)C.C(=O)([O-])[O-].[K+].[K+].BrC=1C=C2C3(C(NC2=CC1)=O)CCCCC3>>O=C1NC2=CC=C(C=C2C12CCCCC2)C=2N(C=CC2)C(=O)OC(C)(C)C | OB(O)[c:12]1[n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:9][cH:10][cH:11]1.Br[c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[C:19]1([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[C:25](=[O:26])[NH:27]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:10][cH:11][c:12]1-[c:13]1[cH:14][cH:15][c:16]2... | CC(C)(C)OC(=O)n1cccc1B(O)O.O=C1Nc2ccc(Br)cc2C12CCCCC2 | CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 | null | null | O | C-C Coupling | Suzuki coupling with boronic acids | 72cb0722e2dfbd8433f7f279041b17208e2a10c7d719ed09e6c4b6dd1c93185b | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccc[nH]3)cc2C12CCCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[#7;a:10]:1-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]>>[C;D1;H3:15]-[C:14](-[C;D1;H3:16])(-[C;D1;H3:17])-[#8:13]-[C:11](=[O;D1;H0:12])-[#7;a:10]1:[c:9]:[c:8]:[c:7]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:1](... | null | [] | 80 | CELSIUS | 15 | MINUTE | To a solution of 5′-bromo-spiro[cyclohexane-1,3′-indolin]-2′-one (3.4 g, 12 mmol) in 1,2-DME (100 mL) under a nitrogen atmosphere was added tetrakis(triphenylphospine)palladium(0) (70 mg, 5 mol %). After 15 min, 2-borono-1H-pyrrole-1-carboxylic acid, 1-tert butyl ester (1.3 eq, 3.31 g, 15.6 mmol) and a solution of K2CO... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCCC1 | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCCC1 | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCCC1 | HBr.B | O | 80 | 0.25 | CC(C)(C)OC(=O)n1cccc1B(O)O.O=C1Nc2ccc(Br)cc2C12CCCCC2>O>CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c3dd858b8414819a8fc99e075305940 | CI.O=C1Nc2ccc(-c3ccc[nH]3)cc2C12CCCCC2>>Cn1cccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 | O.N1C(=CC=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCCC3.C([O-])([O-])=O.[K+].[K+].IC>>CN1C(=CC=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCCC3 | I[CH3:1].[nH:2]1[cH:3][cH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[C:13]1([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[C:19](=[O:20])[NH:21]2>>[CH3:1][n:2]1[cH:3][cH:4][cH:5][c:6]1-[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[C:13]1([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[C:19](=[O:20])[NH:21]2 | CI.O=C1Nc2ccc(-c3ccc[nH]3)cc2C12CCCCC2 | Cn1cccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 | null | null | CCOC(=O)C.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3b0bd5806650bb387428bf36a5e436078e57d40d2afdf9e751829e2a02da9e1d | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=C1Nc2ccc(-c3ccc[nH]3)cc2C12CCCCC2 | 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] | 92.3 | [{"value": 76.0, "product": "CN1C(=CC=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "CN1C(=CC=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 5′-(1H-pyrrole-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one (0.46 g, 1.7 mmol) and potassium carbonate (5 eq, 1.18 g, 8.6 mmol) in DMF (2 mL) at room temperature was treated with a solution of iodomethane (3 eq, 0.32 g, 5.1 mmol) in DMF (1 mL). The solution was stirred 16 h at room temperature, then ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]c1 | c1ccc[nH]1 | c1ccc[nH]1.c1ccc2c(c1)NCC21CCCCC1 | HI | CCOC(=O)C.CN(C)C=O | null | 16 | CI.O=C1Nc2ccc(-c3ccc[nH]3)cc2C12CCCCC2>CCOC(=O)C.CN(C)C=O>Cn1cccc1-c1ccc2c(c1)C1(CCCCC1)C(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ecd93464dc648fe987299a1452499ec | CN(C)C=O.Fc1cc(Br)cc(Br)c1>>O=Cc1cc(F)cc(Br)c1 | CN(C)C=O.BrC=1C=C(C=C(C1)Br)F.C(CCC)[Li]>>FC=1C=C(C=O)C=C(C1)Br | CN(C)[CH:2]=[O:1].Br[c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([Br:9])[cH:10]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([Br:9])[cH:10]1 | CN(C)C=O.Fc1cc(Br)cc(Br)c1 | O=Cc1cc(F)cc(Br)c1 | null | null | C(C)OCC | C-C Coupling | Bouveault aldehyde synthesis | 4664d189e1ff40b394aee0a7d0943c7bfc06c1f81f238cff6865649dda594153 | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-N(-C)-[CH;D2;+0:6]=[O;D1;H0:7]>>[O;D1;H0:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 100 | [{"value": 100.0, "product": "FC=1C=C(C=O)C=C(C1)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3,5-dibromofluorobenzene in diethyl ether (100 cm3) at −78° C. was added n-butyl lithium (2.5 M, 8 cm3, 20 mmol) dropwise. After 30 min. the mixture was treated with DMF (20 cm3) in diethyl ether (10 cm3) and stirring was continued at −78° C. After 30 min. the mixture was quenched with dilute HCl aq., ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)OCC | null | null | CN(C)C=O.Fc1cc(Br)cc(Br)c1>C(C)OCC>O=Cc1cc(F)cc(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-127f208a746641c1877f78d37d4f625e | ON=Cc1cc(F)cc(Br)c1>>N#Cc1cc(F)cc(Br)c1 | FC=1C=C(C=NO)C=C(C1)Br>>FC=1C=C(C#N)C=C(C1)Br | O[N:1]=[CH:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([Br:9])[cH:10]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([Br:9])[cH:10]1 | ON=Cc1cc(F)cc(Br)c1 | N#Cc1cc(F)cc(Br)c1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(C)#N | Functional Group Interconversion | OtherReaction | 17f476cc256704e312f02cdb730538a4d2e78e129aaed9ef4aa555a9b052c890 | 9ad4e779dba60265752423413bc1b61ff9562539f91b24f3b3d9205e4bb46232 | c1ccccc1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 89.3 | [{"value": 89.0, "product": "FC=1C=C(C#N)C=C(C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.3, "product": "FC=1C=C(C#N)C=C(C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | The above oxime (3.76 g, 17.24 mmol) and copper (II) acetate (370 mg) were dissolved in acetonitrile (100 cm3) under nitrogen and heated under reflux. After 5 h, the mixture was evaporated, the residue taken into EtOAc, washed with sulfuric acid (1N), water, brine, dried (MgSO4) and evaporated to give 3-fluoro-5-bromob... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Nitrile | null | null | c1ccccc1 | HO- | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)#N | null | 5 | ON=Cc1cc(F)cc(Br)c1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)#N>N#Cc1cc(F)cc(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb177ac4f5ee408d9791a43cc1ab2c73 | CCOC(OCC)OCC.N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCCC2)C(=O)N3)c1>>CCOC(OCC)N1C(=O)C2(CCCCC2)c2cc(-c3cc(F)cc(C#N)c3)ccc21 | O=C1NC2=CC=C(C=C2C12CCCCC2)C=2C=C(C#N)C=C(C2)F.C(C)OC(OCC)OCC>>C(C)OC(N1C(C2(C3=CC(=CC=C13)C=1C=C(C#N)C=C(C1)F)CCCCC2)=O)OCC | CCO[CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7].[NH:8]1[C:9](=[O:10])[C:11]2([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[c:17]2[cH:18][c:19](-[c:20]3[cH:21][c:22]([F:23])[cH:24][c:25]([C:26]#[N:27])[cH:28]3)[cH:29][cH:30][c:31]21>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[N:8]1[C:9](=[O:10])[C:11]2([CH2:12][CH2:1... | CCOC(OCC)OCC.N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCCC2)C(=O)N3)c1 | CCOC(OCC)N1C(=O)C2(CCCCC2)c2cc(-c3cc(F)cc(C#N)c3)ccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f5b83fcf4b9c65194b6e5c49370fc988f96979e0bef62f46742babca4127b463 | 1ec70821ce282b2f30be459652d8181f281dba872707ca835b3678072970aef7 | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCCC2 | C-C-O-[CH;D3;+0:1](-[#8:2]-[C:3])-[#8:4]-[C:5].[O;D1;H0:6]=[C:7]1-[C:8]-[c:9]:[c:10](:[c:11])-[NH;D2;+0:12]-1>>[C:3]-[#8:2]-[CH;D3;+0:1](-[#8:4]-[C:5])-[N;H0;D3;+0:12]1-[C:7](=[O;D1;H0:6])-[C:8]-[c:9]:[c:10]-1:[c:11] | 56.4 | [{"value": 56.0, "product": "C(C)OC(N1C(C2(C3=CC(=CC=C13)C=1C=C(C#N)C=C(C1)F)CCCCC2)=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.4, "product": "C(C)OC(N1C(C2(C3=CC(=CC=C13)C=1C=C(C#N)C=C(C1)F)CCCCC2)=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(1′,2′-dihydro-2′-oxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-5-flurobenzonitrile (1.0 eq, 0.27 g, 0.84 mmol) in triethylorthoformate (2 mL, 12 mmol) was heated to 150° C. for 1 h. The reaction mixture was allowed to cool, the excess triethylorthoformate was removed in vacuo, and the residue was purifie... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Secondary amide | Ether.Ether.Tertiary amide | c1ccc2c(c1)NCC21CCCCC1 | c1ccc2c(c1)[NH]CC21CCCCC1 | c1ccc2c(c1)[NH]CC21CCCCC1.c1ccccc1 | HO- | null | null | null | CCOC(OCC)OCC.N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCCC2)C(=O)N3)c1>>CCOC(OCC)N1C(=O)C2(CCCCC2)c2cc(-c3cc(F)cc(C#N)c3)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2db3eaaf2bf84fb698ab83a7dad89301 | BrBr.N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCCC2)C(=O)N3)c1>>N#Cc1cc(F)cc(-c2cc(Br)c3c(c2)C2(CCCCC2)C(=O)N3)c1 | BrBr.O=C1NC2=CC=C(C=C2C12CCCCC2)C=2C=C(C#N)C=C(C2)F.C(C)(=O)[O-].[K+]>>BrC=1C=C(C=C2C3(C(NC12)=O)CCCCC3)C=3C=C(C#N)C=C(C3)F | Br[Br:12].[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:13]3[c:14]([cH:15]2)[C:16]2([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[C:22](=[O:23])[NH:24]3)[cH:25]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8](-[c:9]2[cH:10][c:11]([Br:12])[c:13]3[c:14]([cH:15]2)[C:16]2([CH2:17][CH2:18][CH2:19][CH2... | BrBr.N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCCC2)C(=O)N3)c1 | N#Cc1cc(F)cc(-c2cc(Br)c3c(c2)C2(CCCCC2)C(=O)N3)c1 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | b75a0cb1be6e87ac5ae2a0c4fc61b176231cdf76c6a5c5e00ef053906cd4efba | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCCC2 | Br-[Br;H0;D1;+0:1].[O;D1;H0:2]=[C:3]-[#7:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](:[c:6])-[#7:4]-[C:3]=[O;D1;H0:2] | 43 | [{"value": 43.0, "product": "BrC=1C=C(C=C2C3(C(NC12)=O)CCCCC3)C=3C=C(C#N)C=C(C3)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.8, "product": "BrC=1C=C(C=C2C3(C(NC12)=O)CCCCC3)C=3C=C(C#N)C=C(C3)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 3-(1′,2′-dihydro-2′-oxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-5-fluorobenzonitrile (0.40 g, 1.23 mmol) and potassium acetate (0.13 g, 1.3 mmol) in glacial acetic acid (3 mL) at room temperature was treated with a solution of bromine (1.05 eq, 0.21 g, 1.3 mmol) in a glacial acetic acid (3 mL). After stirr... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)NCC21CCCCC1 | c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | HBr | C(C)(=O)O | null | 1 | BrBr.N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCCC2)C(=O)N3)c1>C(C)(=O)O>N#Cc1cc(F)cc(-c2cc(Br)c3c(c2)C2(CCCCC2)C(=O)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-967eab84cf294f14a5ffbf24e2df570b | N#Cc1cc(F)cc(-c2cc([N+](=O)[O-])c3c(c2)C2(CCCCC2)C(=O)N3)c1>>N#Cc1cc(F)cc(-c2cc(N)c3c(c2)C2(CCCCC2)C(=O)N3)c1 | CCOCC.[N+](=O)([O-])C=1C=C(C=C2C3(C(NC12)=O)CCCCC3)C=3C=C(C#N)C=C(C3)F.O.O.[Sn](Cl)Cl>>NC=1C=C(C=C2C3(C(NC12)=O)CCCCC3)C=3C=C(C#N)C=C(C3)F | O=[N+:12]([O-])[c:11]1[cH:10][c:9](-[c:8]2[cH:7][c:5]([F:6])[cH:4][c:3]([C:2]#[N:1])[cH:25]2)[cH:15][c:14]2[c:13]1[NH:24][C:22](=[O:23])[C:16]21[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8](-[c:9]2[cH:10][c:11]([NH2:12])[c:13]3[c:14]([cH:15]2)[C:16]2([CH2:17][CH2:18][CH2:19][... | N#Cc1cc(F)cc(-c2cc([N+](=O)[O-])c3c(c2)C2(CCCCC2)C(=O)N3)c1 | N#Cc1cc(F)cc(-c2cc(N)c3c(c2)C2(CCCCC2)C(=O)N3)c1 | null | null | C(C)(=O)O.Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCCC2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[#7:5]>>[#7:5]-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 52.2 | [{"value": 50.0, "product": "NC=1C=C(C=C2C3(C(NC12)=O)CCCCC3)C=3C=C(C#N)C=C(C3)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "NC=1C=C(C=C2C3(C(NC12)=O)CCCCC3)C=3C=C(C#N)C=C(C3)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 3-(7′-nitro-1′,2′-dihydro-2′-oxospiro-[cyclohexane-1,3′-[3H]indol]-5′-yl)-5-fluorobenzonitrile (1.0 eq, 0.16 g, 0.4 mmol) in glacial acetic acid (4 mL) at room temperature was added a solution of tin (11) chloride dihydrate (0.25 g, 1.1 mmol) in hydrochloric acid (2 mL). The yellow mixture was boiled f... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | Other | C(C)(=O)O.Cl | null | 0.5 | N#Cc1cc(F)cc(-c2cc([N+](=O)[O-])c3c(c2)C2(CCCCC2)C(=O)N3)c1>C(C)(=O)O.Cl>N#Cc1cc(F)cc(-c2cc(N)c3c(c2)C2(CCCCC2)C(=O)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ec30d5d8d36b4660ac9a6f7ed422bbdc | CC1(C)CC(=O)OC(=O)C1>>CC(C)(CCO)CCO | CC1(CC(=O)OC(C1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>CC(CCO)(CCO)C | O=[C:8]1[CH2:7][C:2]([CH3:1])([CH3:3])[CH2:4][C:5](=[O:6])[O:9]1>>[CH3:1][C:2]([CH3:3])([CH2:4][CH2:5][OH:6])[CH2:7][CH2:8][OH:9] | CC1(C)CC(=O)OC(=O)C1 | CC(C)(CCO)CCO | null | null | C1CCOC1 | Reduction | OtherReaction | f12eb5c735bf32cc6e26e27e77389d0bf7d3c87ff0801ff11a8982e2614ac159 | 62efeb05e7838a098a8a3af9d4f83fa4539c6fc2ad44bda3a588044dee3bd05e | null | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[O;H0;D2;+0:7]-1>>[OH;D1;+0:6]-[CH2;D2;+0:5]-[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[OH;D1;+0:7] | null | [] | null | null | 3 | HOUR | A solution of 3,3-dimethylglutaric anhydride in dry THF (60 cm3) was added over 30 min. to lithium aluminum hydride in dry THF (300 cm3) under nitrogen at 0° C. The mixture was then brought gradually up-to reflux. After 3 h, the mixture was cooled, treated with water (3.3 cm3), sodium hydroxide solution (15%, 3.3 cm3) ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Primary alcohol.Primary alcohol | C1CCOCC1 | null | null | Other | C1CCOC1 | null | 3 | CC1(C)CC(=O)OC(=O)C1>C1CCOC1>CC(C)(CCO)CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d1e1c94f9dc64c0087543e505f1ab4ee | N#Cc1ccc(Br)cc1F.O=C1Nc2ccccc2C12CCCC(B(O)O)C2>>N#Cc1ccc(-c2ccc3c(c2)C2(CCCCC2)C(=O)N3)cc1F | [OH-].[Na+].C(#N)C1=C(C=C(C=C1)Br)F.N1C(C2(C3=CC=CC=C13)CCCC(C2)B(O)O)=O.C(C)(=O)[O-].[Na+]>>C(#N)C1=C(C=C(C=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCCC3)F | Br[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[c:23]([F:24])[cH:22]1.OB(O)[CH:15]1[CH2:14][C:13]2([c:11]3[c:10]([cH:9][cH:8][cH:7][cH:12]3)[NH:21][C:19]2=[O:20])[CH2:18][CH2:17][CH2:16]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[C:13]2([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:19](=[O:20... | N#Cc1ccc(Br)cc1F.O=C1Nc2ccccc2C12CCCC(B(O)O)C2 | N#Cc1ccc(-c2ccc3c(c2)C2(CCCCC2)C(=O)N3)cc1F | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | OtherReaction | 8734c5dd9f1a6e6409bcbbc53c99a0241dd1b8ab9806eccd050fa6b5202b7ad6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[CH;D3;+0:6](-[C:7]-[C:8](-[c:9]:[c:10]:[cH;D2;+0:11]:[c:12]:[c:13])-[C:14](=[O;D1;H0:15])-[#7:16])-[C:17]-[C:18]>>[#7:16]-[C:14](=[O;D1;H0:15])-[C:8](-[C:7]-[CH2;D2;+0:6]-[C:17]-[C:18])-[c:9]:[c:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:12]:[c... | 37 | [{"value": 37.0, "product": "C(#N)C1=C(C=C(C=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCCC3)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.0, "product": "C(#N)C1=C(C=C(C=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCCC3)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-cyano-3-fluoro-bromobenzene (0.76 g, 3.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.3 g) in ethylene glycol dimethyl ether (15 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (1.4 g, 5.7 mmol) and sodi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | N#Cc1ccc(Br)cc1F.O=C1Nc2ccccc2C12CCCC(B(O)O)C2>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>N#Cc1ccc(-c2ccc3c(c2)C2(CCCCC2)C(=O)N3)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0661f7b16f034407b75a2e89db679842 | CC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1ccc(F)c(Cl)c1>>CC1(C)C(=O)Nc2ccc(-c3ccc(F)c(Cl)c3)cc21 | [Cl-].[NH4+].BrC=1C=C2C(C(NC2=CC1)=O)(C)C.ClC=1C=C(C=CC1F)B(O)O.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C=CC1F)C=1C=C2C(C(NC2=CC1)=O)(C)C | Br[c:10]1[cH:9][cH:8][c:7]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[C:4](=[O:5])[NH:6]2.OB(O)[c:11]1[cH:12][cH:13][c:14]([F:15])[c:16]([Cl:17])[cH:18]1>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([F:15])[c:16]([Cl:17])[cH:18]3)[cH:19][c:20]21 | CC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1ccc(F)c(Cl)c1 | CC1(C)C(=O)Nc2ccc(-c3ccc(F)c(Cl)c3)cc21 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O.C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 9791290dea007c134587598bd16674eb122eb7281e427c61b6d8f55d72a5f584 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccccc3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 30 | [{"value": 30.0, "product": "ClC=1C=C(C=CC1F)C=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.5, "product": "ClC=1C=C(C=CC1F)C=1C=C2C(C(NC2=CC1)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-bromo-3,3-dimethyl-1,3-dihydro-indol-2-one (0.35 g, 1.46 mmol) and tetrakis(triphenylphosphine) palladium (0.13 g, 0.11 mmol) in dimethoxyethane (10 cm3) was stirred under N2 for 20 min. To this mixture was then added 3-chloro-4-fluorobenzene boronic acid (0.26 g, 1.49 mmol) and potassium carbonate (0.6... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.C(OC)COC | null | null | CC1(C)C(=O)Nc2ccc(Br)cc21.OB(O)c1ccc(F)c(Cl)c1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.C(OC)COC>CC1(C)C(=O)Nc2ccc(-c3ccc(F)c(Cl)c3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6c9ebd1225d4262acc61210cf49b56e | COC(OC)OC.O=C(O)c1cccc(Br)c1F>>COC(=O)c1cccc(Br)c1F | BrC=1C(=C(C(=O)O)C=CC1)F.COC(OC)OC.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrC=1C(=C(C(=O)OC)C=CC1)F | COC(OC)O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[c:11]1[F:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[c:11]1[F:12] | COC(OC)OC.O=C(O)c1cccc(Br)c1F | COC(=O)c1cccc(Br)c1F | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | e4ba447406da54314398d95bd1b71f2d2399894b79239d67c6492adcfcb5be5b | febd4a5f8968afbe4e7e6fe21028d84a656200d2366551d30fab5764938f4b3b | c1ccccc1 | C-O-C(-O-C)-O-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 84 | [{"value": 84.0, "product": "BrC=1C(=C(C(=O)OC)C=CC1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "BrC=1C(=C(C(=O)OC)C=CC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol (5 ml) under nitrogen was treated with trimethylorthoformate (0.22 ml, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether.Ether | Ester | null | null | c1ccccc1 | HO- | CO | null | 16 | COC(OC)OC.O=C(O)c1cccc(Br)c1F>CO>COC(=O)c1cccc(Br)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f67eb7b38921421f80388afa72539b7c | O=C1Nc2ccccc2C12CCCC(B(O)O)C2.ON=Cc1cccc(Br)c1F>>O=C1Nc2ccc(-c3cccc(C=NO)c3F)cc2C12CCCCC2 | BrC=1C(=C(C=NO)C=CC1)F.N1C(C2(C3=CC=CC=C13)CCCC(C2)B(O)O)=O>>FC1=C(C=NO)C=CC=C1C=1C=C2C3(C(NC2=CC1)=O)CCCCC3 | OB(O)[CH:24]1[CH2:23][CH2:22][CH2:21][C:20]2([C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:18][c:19]32)[CH2:25]1.Br[c:8]1[cH:9][cH:10][cH:11][c:12]([CH:13]=[N:14][OH:15])[c:16]1[F:17]>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12]([CH:13]=[N:14][OH:15])[c:16]3[F:17])[cH:18][c:19]2[C:20]12... | O=C1Nc2ccccc2C12CCCC(B(O)O)C2.ON=Cc1cccc(Br)c1F | O=C1Nc2ccc(-c3cccc(C=NO)c3F)cc2C12CCCCC2 | null | null | null | C-C Coupling | OtherReaction | 8734c5dd9f1a6e6409bcbbc53c99a0241dd1b8ab9806eccd050fa6b5202b7ad6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].O-B(-O)-[CH;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11](-[c:12]:[c:13]:[cH;D2;+0:14]:[c:15]:[c:16])-[C:17](=[O;D1;H0:18])-[#7:19]>>[#7:19]-[C:17](=[O;D1;H0:18])-[C:11](-[C:10]-[CH2;D2;+0:7]-[C:8]-[C:9])-[c:12]:[c:13]:[c;H0;D3;+0:14](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](... | 15 | [{"value": 15.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 3-bromo-2-fluorobenzaldoxime (0.40 g, 1.83 mmol) and (spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid as described in example 18, to afford the product (0.094 g, 0.27 mmol, 15% yield) as a white solid: mp. 213–217° C.; 1H NMR (CDCl3) δ 10.95 (s, 1H), 9.65 (s, 1H), 8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)NCC21CCCCC1.c1ccccc1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCCC1 | HBr.B | null | null | null | O=C1Nc2ccccc2C12CCCC(B(O)O)C2.ON=Cc1cccc(Br)c1F>>O=C1Nc2ccc(-c3cccc(C=NO)c3F)cc2C12CCCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e736cd9e5dfa4540856d7ba0972deb9f | CN(C)C=O.Cc1ccsc1Br>>Cc1cc(C=O)sc1Br | BrC=1SC=CC1C.C(C)NCC.[Li]CCCC.CN(C)C=O>>BrC1=C(C=C(S1)C=O)C | CN(C)[CH:5]=[O:6].[CH3:1][c:2]1[cH:3][cH:4][s:7][c:8]1[Br:9]>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]=[O:6])[s:7][c:8]1[Br:9] | CN(C)C=O.Cc1ccsc1Br | Cc1cc(C=O)sc1Br | null | null | C1CCOC1.CCCCCC | C-C Coupling | OtherReaction | 77a8917ac8ed8f2ad464b767187c983c24a719c711c4936bfe09b270792882f5 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccsc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[#16;a:3]1:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:7]1:[#16;a:3]:[c:4]:[c:5]:[c:6]:1 | 88.3 | [{"value": 88.3, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | -40 | CELSIUS | 30 | MINUTE | To a solution of diethylamine (28 g, 0.383 mol) in anhydrous THF (400 mL) was added at −40° C. under nitrogen a solution of n-BuLi (2.5 M, 153 mL, 0.383 mol) in hexane. After addition, the solution was stirred at −40° C. under nitrogen for 30 minutes, cooled to −78° C. and treated dropwise with a solution of 2-bromo-3-... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccsc1 | c1ccsc1 | c1ccsc1 | Other | C1CCOC1.CCCCCC | -40 | 0.5 | CN(C)C=O.Cc1ccsc1Br>C1CCOC1.CCCCCC>Cc1cc(C=O)sc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed84227053dd4cc8ab8a2904657eb785 | CC(C)OB(OC(C)C)OC(C)C.O=C1Nc2ccccc2C12CCCC2Br>>O=C1Nc2ccccc2C12CCCC2B(O)O | C(C)(C)OB(OC(C)C)OC(C)C.BrC1CCCC12C(NC1=CC=CC=C21)=O.[H-].[Na+].Cl.C(CCC)[Li]>>N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O | CC(C)O[B:15]([O:16]C(C)C)[O:17]C(C)C.Br[CH:14]1[C:10]2([C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:8][c:9]32)[CH2:11][CH2:12][CH2:13]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[C:10]12[CH2:11][CH2:12][CH2:13][CH:14]2[B:15]([OH:16])[OH:17] | CC(C)OB(OC(C)C)OC(C)C.O=C1Nc2ccccc2C12CCCC2Br | O=C1Nc2ccccc2C12CCCC2B(O)O | null | null | C1CCOC1 | Miscellaneous | Preparation of boronic acids | bca11e30670273bc6ec323b03c7ec227f7adab5fe1829cec8213e51049a9b3c9 | 439f75838a365ac96edb92157a4b914b608bcaa4f1e95debd26b1d95d818cefc | O=C1Nc2ccccc2C12CCCC2 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-12-[c:6]:[c:7]-[#7:8]-[C:9]-2=[O;D1;H0:10].C-C(-C)-O-[B;H0;D3;+0:11](-[O;H0;D2;+0:12]-C(-C)-C)-[O;H0;D2;+0:13]-C(-C)-C>>[O;D1;H0:10]=[C:9]1-[#7:8]-[c:7]:[c:6]-[C:5]-12-[C:4]-[C:3]-[C:2]-[CH;D3;+0:1]-2-[B;H0;D3;+0:11](-[OH;D1;+0:12])-[OH;D1;+0:13] | 64 | [{"value": 64.0, "product": "N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.7, "product": "N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of 5-bromo-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (13.1 g, 53 mmol) in anhydrous THF (300 cm3) under N2, was added sodium hydride (60% in mineral oil, 2.1 g, 53 mmol). After 30 minutes, the reaction mixture was cooled to −78° C. and butyl lithium (2.5 M in hexanes, 22 cm3, 53 mmol) was added slowl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | Boronic acid | c1ccc2c(c1)NCC21CCCC1 | c1ccc2c(c1)NCC21CCCC1 | c1ccc2c(c1)NCC21CCCC1 | HBr | C1CCOC1 | -78 | 0.5 | CC(C)OB(OC(C)C)OC(C)C.O=C1Nc2ccccc2C12CCCC2Br>C1CCOC1>O=C1Nc2ccccc2C12CCCC2B(O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3151ca8d5834466e9951742a23165a9c | N#Cc1ccc(Br)cc1F.O=C1Nc2ccccc2C12CCCC2B(O)O>>N#Cc1ccc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)cc1F | [OH-].[Na+].C(#N)C1=C(C=C(C=C1)Br)F.N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O.C([O-])([O-])=O.[Na+].[Na+]>>C(#N)C1=C(C=C(C=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCC3)F | Br[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[c:22]([F:23])[cH:21]1.OB(O)[CH:17]1[C:13]2([c:11]3[c:10]([cH:9][cH:8][cH:7][cH:12]3)[NH:20][C:18]2=[O:19])[CH2:14][CH2:15][CH2:16]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[C:13]2([CH2:14][CH2:15][CH2:16][CH2:17]2)[C:18](=[O:19])[NH:20]3)[cH:2... | N#Cc1ccc(Br)cc1F.O=C1Nc2ccccc2C12CCCC2B(O)O | N#Cc1ccc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)cc1F | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | OtherReaction | 730dcdc10a1abdabad91331a2b6e5cbbf0777aa3d68588c0d603eed6404753ea | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[CH;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10]-12-[C:11](=[O;D1;H0:12])-[#7:13]-[c:14]1:[c:15]:[c:16]:[cH;D2;+0:17]:[c:18]:[c:19]:1-2>>[O;D1;H0:12]=[C:11]1-[#7:13]-[c:14]2:[c:15]:[c:16]:[c;H0;D3;+0:17](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:18]:[c:19]:2-[C:10]-12-[C:9]... | 36.9 | [{"value": 36.0, "product": "C(#N)C1=C(C=C(C=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCC3)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.9, "product": "C(#N)C1=C(C=C(C=C1)C=1C=C2C3(C(NC2=CC1)=O)CCCC3)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-cyano-3-fluoro-bromobenzene (0.63 g, 3.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (1.0 g, 4.7 mmol) and sod... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | N#Cc1ccc(Br)cc1F.O=C1Nc2ccccc2C12CCCC2B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>N#Cc1ccc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5da18c4b6b945759ba515164e6f2ac3 | N#Cc1cc(Br)ccc1F.O=C1Nc2ccccc2C12CCCC2B(O)O>>N#Cc1cc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)ccc1F | [OH-].[Na+].C(#N)C=1C=C(C=CC1F)Br.N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O.C(C)(=O)[O-].[Na+]>>C(#N)C=1C=C(C=CC1F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3 | Br[c:5]1[cH:4][c:3]([C:2]#[N:1])[c:22]([F:23])[cH:21][cH:20]1.OB(O)[CH:16]1[C:12]2([c:10]3[c:9]([cH:8][cH:7][cH:6][cH:11]3)[NH:19][C:17]2=[O:18])[CH2:13][CH2:14][CH2:15]1>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[C:12]2([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:17](=[O:18])[NH:19]3)[cH:20][cH:2... | N#Cc1cc(Br)ccc1F.O=C1Nc2ccccc2C12CCCC2B(O)O | N#Cc1cc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)ccc1F | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | OtherReaction | 730dcdc10a1abdabad91331a2b6e5cbbf0777aa3d68588c0d603eed6404753ea | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[CH;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10]-12-[C:11](=[O;D1;H0:12])-[#7:13]-[c:14]1:[c:15]:[c:16]:[cH;D2;+0:17]:[c:18]:[c:19]:1-2>>[O;D1;H0:12]=[C:11]1-[#7:13]-[c:14]2:[c:15]:[c:16]:[c;H0;D3;+0:17](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:18]:[c:19]:2-[C:10]-12-[C:9]... | 10.5 | [{"value": 10.0, "product": "C(#N)C=1C=C(C=CC1F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.5, "product": "C(#N)C=1C=C(C=CC1F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-cyano-4-fluoro-bromobenzene (0.63 g, 3.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (1.0 g, 4.7 mmol) and sod... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | N#Cc1cc(Br)ccc1F.O=C1Nc2ccccc2C12CCCC2B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>N#Cc1cc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4bb3309a143643eba7901a508b43c68d | Fc1ccc(Br)cc1Cl.O=C1Nc2ccccc2C12CCCC2B(O)O>>O=C1Nc2ccc(-c3ccc(F)c(Cl)c3)cc2C12CCCC2 | [OH-].[Na+].ClC=1C=C(C=CC1F)Br.N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O.C([O-])([O-])=O.[Na+].[Na+]>>ClC=1C=C(C=CC1F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3 | Br[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([Cl:14])[cH:15]1.OB(O)[CH:22]1[C:18]2([C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][cH:16][c:17]32)[CH2:19][CH2:20][CH2:21]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([F:12])[c:13]([Cl:14])[cH:15]3)[cH:16][c:17]2[C:18]12[CH2:19][CH2:20][CH2:21][CH2:22]... | Fc1ccc(Br)cc1Cl.O=C1Nc2ccccc2C12CCCC2B(O)O | O=C1Nc2ccc(-c3ccc(F)c(Cl)c3)cc2C12CCCC2 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | OtherReaction | 730dcdc10a1abdabad91331a2b6e5cbbf0777aa3d68588c0d603eed6404753ea | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[CH;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10]-12-[C:11](=[O;D1;H0:12])-[#7:13]-[c:14]1:[c:15]:[c:16]:[cH;D2;+0:17]:[c:18]:[c:19]:1-2>>[O;D1;H0:12]=[C:11]1-[#7:13]-[c:14]2:[c:15]:[c:16]:[c;H0;D3;+0:17](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:18]:[c:19]:2-[C:10]-12-[C:9]... | 66.4 | [{"value": 66.0, "product": "ClC=1C=C(C=CC1F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.4, "product": "ClC=1C=C(C=CC1F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-chloro-4-fluoro-bromobenzene (0.4 cm3, 0.66 g, 3.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (1.0 g, 4.7 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | Fc1ccc(Br)cc1Cl.O=C1Nc2ccccc2C12CCCC2B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>O=C1Nc2ccc(-c3ccc(F)c(Cl)c3)cc2C12CCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc8c2eefce194c1cbba27d8811aed3e9 | N#Cc1cccc(Br)c1.O=C1Nc2ccccc2C12CCCC2B(O)O>>N#Cc1cccc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)c1 | [OH-].[Na+].BrC=1C=C(C#N)C=CC1.N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O.C([O-])([O-])=O.[Na+].[Na+]>>C(#N)C=1C=C(C=CC1)C=1C=C2C3(C(NC2=CC1)=O)CCCC3 | Br[c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:22]1.OB(O)[CH:18]1[C:14]2([c:12]3[c:11]([cH:10][cH:9][cH:8][cH:13]3)[NH:21][C:19]2=[O:20])[CH2:15][CH2:16][CH2:17]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[C:14]2([CH2:15][CH2:16][CH2:17][CH2:18]2)[C:19](=[O:20])[NH:21]3)[cH:2... | N#Cc1cccc(Br)c1.O=C1Nc2ccccc2C12CCCC2B(O)O | N#Cc1cccc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | OtherReaction | 730dcdc10a1abdabad91331a2b6e5cbbf0777aa3d68588c0d603eed6404753ea | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[CH;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10]-12-[C:11](=[O;D1;H0:12])-[#7:13]-[c:14]1:[c:15]:[c:16]:[cH;D2;+0:17]:[c:18]:[c:19]:1-2>>[O;D1;H0:12]=[C:11]1-[#7:13]-[c:14]2:[c:15]:[c:16]:[c;H0;D3;+0:17](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:18]:[c:19]:2-[C:10]-12-[C:9]... | 40 | [{"value": 40.0, "product": "C(#N)C=1C=C(C=CC1)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.0, "product": "C(#N)C=1C=C(C=CC1)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-bromobenzonitrile (0.5 g, 2.6 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (0.9 g, 3.9 mmol) and sodium carbona... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | N#Cc1cccc(Br)c1.O=C1Nc2ccccc2C12CCCC2B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>N#Cc1cccc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9efd0e3ceac474680ddb105e57d88d7 | N#Cc1ccc(Br)o1.O=C1Nc2ccccc2C12CCCC2B(O)O>>CC1(C)C(=O)Nc2ccc(-c3ccc(C#N)o3)cc21 | [OH-].[Na+].C(#N)C1=CC=C(O1)Br.N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O.C([O-])([O-])=O.[Na+].[Na+]>>CC1(C(NC2=CC=C(C=C12)C1=CC=C(O1)C#N)=O)C | Br[c:11]1[cH:12][cH:13][c:14]([C:15]#[N:16])[o:17]1.OB(O)[CH:3]1CC[CH2:1][C:2]12[C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][cH:18][c:19]12>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]#[N:16])[o:17]3)[cH:18][c:19]21 | N#Cc1ccc(Br)o1.O=C1Nc2ccccc2C12CCCC2B(O)O | CC1(C)C(=O)Nc2ccc(-c3ccc(C#N)o3)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.COCCOC | C-C Coupling | OtherReaction | 56f456838de89c8a0040f39210a739b1648612eed6c31bebe31156c0fd5026ae | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Cc2cc(-c3ccco3)ccc2N1 | Br-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.O-B(-O)-[CH;D3;+0:6]1-C-C-[CH2;D2;+0:7]-[C:8]-12-[C:9](=[O;D1;H0:10])-[#7:11]-[c:12]1:[c:13]:[c:14]:[cH;D2;+0:15]:[c:16]:[c:17]:1-2>>[CH3;D1;+0:7]-[C:8]1(-[CH3;D1;+0:6])-[C:9](=[O;D1;H0:10])-[#7:11]-[c:12]2:[c:13]:[c:14]:[c;H0;D3;+0:15](-[c;H0;D3;+0:1]3:[#8;a:2]:[c:3]:[c:... | 53.4 | [{"value": 49.0, "product": "CC1(C(NC2=CC=C(C=C12)C1=CC=C(O1)C#N)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.4, "product": "CC1(C(NC2=CC=C(C=C12)C1=CC=C(O1)C#N)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-cyano-2-bromofuran (0.5 g, 2.6 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (0.9 g, 3.9 mmol) and sodium carbon... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccoc1.c1ccc2c(c1)NCC21CCCC1 | c1ccc2c(c1)CCN2.c1ccoc1 | c1ccc2c(c1)CCN2.c1ccoc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | N#Cc1ccc(Br)o1.O=C1Nc2ccccc2C12CCCC2B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>CC1(C)C(=O)Nc2ccc(-c3ccc(C#N)o3)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc1c25ef113c4312b9b8cac18149bd88 | N#Cc1cc(F)cc(Br)c1.O=C1Nc2ccccc2C12CCCC2B(O)O>>N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)c1 | [OH-].[Na+].C(#N)C=1C=C(C=C(C1)F)Br.N1C(C2(C3=CC=CC=C13)CCCC2B(O)O)=O.C([O-])([O-])=O.[Na+].[Na+]>>C(#N)C=1C=C(C=C(C1)F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3 | Br[c:8]1[cH:7][c:5]([F:6])[cH:4][c:3]([C:2]#[N:1])[cH:23]1.OB(O)[CH:19]1[C:15]2([c:13]3[c:12]([cH:11][cH:10][cH:9][cH:14]3)[NH:22][C:20]2=[O:21])[CH2:16][CH2:17][CH2:18]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[C:15]2([CH2:16][CH2:17][CH2:18][CH2:19]2)[C:20](=[O:21])... | N#Cc1cc(F)cc(Br)c1.O=C1Nc2ccccc2C12CCCC2B(O)O | N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | OtherReaction | 730dcdc10a1abdabad91331a2b6e5cbbf0777aa3d68588c0d603eed6404753ea | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2C12CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[CH;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10]-12-[C:11](=[O;D1;H0:12])-[#7:13]-[c:14]1:[c:15]:[c:16]:[cH;D2;+0:17]:[c:18]:[c:19]:1-2>>[O;D1;H0:12]=[C:11]1-[#7:13]-[c:14]2:[c:15]:[c:16]:[c;H0;D3;+0:17](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:18]:[c:19]:2-[C:10]-12-[C:9]... | 44 | [{"value": 44.0, "product": "C(#N)C=1C=C(C=C(C1)F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.9, "product": "C(#N)C=1C=C(C=C(C1)F)C=1C=C2C3(C(NC2=CC1)=O)CCCC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-cyano-5-fluoro-bromobenzene (0.5 g, 2.6 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (0.9 g, 3.9 mmol) and sodi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | c1ccccc1.c1ccc2c(c1)NCC21CCCC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | null | null | N#Cc1cc(F)cc(Br)c1.O=C1Nc2ccccc2C12CCCC2B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>N#Cc1cc(F)cc(-c2ccc3c(c2)C2(CCCC2)C(=O)N3)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b337e6af2f0449cad27ae97895f7ad8 | O=C(N[C@@H]1CCCC[C@@H]1C(=O)O)c1ccccc1>>N[C@@H]1CCCC[C@@H]1C(=O)O | C(C1=CC=CC=C1)(=O)N[C@H]1[C@H](CCCC1)C(=O)O>>N[C@H]1[C@H](CCCC1)C(=O)O | O=C(c1ccccc1)[NH:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[C:8](=[O:9])[OH:10]>>[NH2:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[C:8](=[O:9])[OH:10] | O=C(N[C@@H]1CCCC[C@@H]1C(=O)O)c1ccccc1 | N[C@@H]1CCCC[C@@H]1C(=O)O | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | b3a2466df64e83088d842fa3b84d9d4c5dc7cf4647982ead4c7f13c216c92e77 | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | C1CCCCC1 | O=C(-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7])-c1:c:c:c:c:c:1>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | null | null | null | null | A mixture of (+)-(1S,2R)-2-benzamidocyclohexanecarboxylic acid (4.0 g, 16.2 mmol, TCI chemical company) and 6 M hydrochloric acid (200 mL) was heated at reflux for 48 h. The reaction mixture was cooled to room temperature and extracted with diethyl ether (2×200 mL). The aqueous portion was concentrated in vacuo to affo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | c1ccccc1 | null | C1CCCCC1 | HO- | Cl | null | null | O=C(N[C@@H]1CCCC[C@@H]1C(=O)O)c1ccccc1>Cl>N[C@@H]1CCCC[C@@H]1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc8ca99006cd4d0180935677cde6acc1 | CO.N[C@@H]1CCCC[C@@H]1C(=O)O>>COC(=O)[C@H]1CCCC[C@H]1N | N[C@H]1[C@H](CCCC1)C(=O)O.CO.S(=O)(Cl)Cl>>COC(=O)[C@@H]1[C@@H](CCCC1)N | [CH3:1][OH:2].O[C:3](=[O:4])[C@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]1[NH2:11]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]1[NH2:11] | CO.N[C@@H]1CCCC[C@@H]1C(=O)O | COC(=O)[C@H]1CCCC[C@H]1N | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | C1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C;D1;H3:6])-[C:5] | null | [] | null | null | 24 | HOUR | Thionyl chloride (4.73 mL, 64.8 mmol) was slowly added to a chilled (ice-water bath) suspension of (1S,2R)-2-aminocyclohexanecarboxylic acid (16.2 mmol) in anhydrous methanol (200 mL). After complete addition, the cold bath was removed and the resulting mixture warmed to room temperature. After 24 h, the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | C1CCCCC1 | HO- | null | null | 24 | CO.N[C@@H]1CCCC[C@@H]1C(=O)O>>COC(=O)[C@H]1CCCC[C@H]1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bcf6bf420bc14bbda24033646b1b1b0a | CO.N[C@H]1CCCC[C@H]1C(=O)O>>COC(=O)[C@@H]1CCCC[C@@H]1N | S(=O)(Cl)Cl.N[C@@H]1[C@@H](CCCC1)C(=O)O.CO>>COC(=O)[C@H]1[C@H](CCCC1)N | [CH3:1][OH:2].O[C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[NH2:11]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[NH2:11] | CO.N[C@H]1CCCC[C@H]1C(=O)O | COC(=O)[C@@H]1CCCC[C@@H]1N | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | C1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C;D1;H3:6])-[C:5] | null | [] | null | null | 18 | HOUR | Thionyl chloride (5.48 g, 46.1 mmol) was added dropwise to a solution of cis-2-aminocyclohexanecarboxylic acid (2.0 g, 14.0 mmol) in methanol (50 mL) at 0° C. The mixture was allowed to warm to room temperature and stir for 18 h. The clear solution was then evaporated to dryness, and the residual volatiles were removed... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | C1CCCCC1 | HO- | null | null | 18 | CO.N[C@H]1CCCC[C@H]1C(=O)O>>COC(=O)[C@@H]1CCCC[C@@H]1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e56c1f2df7514a04a72d834c171ea357 | N[C@H]1CCCCC[C@H]1C(=O)O>>COC(=O)[C@@H]1CCCCC[C@@H]1N | Cl[Si](C)(C)C.N[C@@H]1[C@@H](CCCCC1)C(=O)O>>COC(=O)[C@H]1[C@H](CCCCC1)N | [OH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[NH2:12]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[NH2:12] | N[C@H]1CCCCC[C@H]1C(=O)O | COC(=O)[C@@H]1CCCCC[C@@H]1N | null | null | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | C1CCCCCC1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C;D1;H3:5] | 61.8 | [{"value": 61.8, "product": "COC(=O)[C@H]1[C@H](CCCCC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Chlorotrimethylsilane (3.96 mL, 31.2 mmol) was added dropwise to cis-2-aminocycloheptanecarboxylic acid (2.45 g, 15.6 mmol) in methanol (25 mL) at room temperature under nitrogen. After stirring for 2 h, the solvent was evaporated in vacuo and the residue was triturated with ether. The white solid was filtered and then... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | C1CCCCCC1 | Other | CO | null | 2 | N[C@H]1CCCCC[C@H]1C(=O)O>CO>COC(=O)[C@@H]1CCCCC[C@@H]1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-57e931ed8b40432a8e566050afde8884 | COC(=O)[C@H]1CCCC[C@H]1N.N>>NC(=O)[C@H]1CCCC[C@H]1N | COC(=O)[C@@H]1[C@@H](CCCC1)N.N>>N[C@H]1[C@H](CCCC1)C(=O)N | CO[C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH2:10].[NH3:1]>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH2:10] | COC(=O)[C@H]1CCCC[C@H]1N.N | NC(=O)[C@H]1CCCC[C@H]1N | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | C1CCCCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH3;D0;+0:6]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:6])=[O;D1;H0:2])-[C:5] | null | [] | null | null | 24 | HOUR | A mixture of (1S,2R)-2-aminocyclohexanecarboxylic acid methyl ester (16.2 mmol) and aqueous ammonia (28%, 50 mL) was stirred at room temperature for 24 h. The reaction mixture was concentrated to dryness in vacuo. The residue was suspended in toluene (200 mL) and reconcentrated to afford (1S,2R)-2-aminocyclohexanecarbo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | C1CCCCC1 | HO- | null | null | 24 | COC(=O)[C@H]1CCCC[C@H]1N.N>>NC(=O)[C@H]1CCCC[C@H]1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc1c3c23629140928ac9e042705804cc | COC(=O)[C@@H]1CCCC[C@@H]1N.[NH4+]>>NC(=O)[C@@H]1CCCC[C@@H]1N | COC(=O)[C@H]1[C@H](CCCC1)N.[OH-].[NH4+]>>N[C@@H]1[C@@H](CCCC1)C(=O)N | CO[C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH2:10].[NH4+:1]>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH2:10] | COC(=O)[C@@H]1CCCC[C@@H]1N.[NH4+] | NC(=O)[C@@H]1CCCC[C@@H]1N | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | C1CCCCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH4+;D0:6]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:6])=[O;D1;H0:2])-[C:5] | null | [] | null | null | 16 | HOUR | cis-2-Aminocyclohexanecarboxylic acid methyl ester (2.20 g, 14.0 mmol) was treated with aqueous ammonium hydroxide (40 mL) in toluene (40 mL) and stirred vigorously at room temperature for 16 h. The reaction was concentrated to dryness in vacuo and azeotroped with toluene (50 mL). The crude product, cis-2-aminocyclohex... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | C1CCCCC1 | HO- | C1(=CC=CC=C1)C | null | 16 | COC(=O)[C@@H]1CCCC[C@@H]1N.[NH4+]>C1(=CC=CC=C1)C>NC(=O)[C@@H]1CCCC[C@@H]1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02ef1dfe6f1a403686e87c22720d628b | COC(=O)[C@@H]1CCCCC[C@@H]1N.[NH4+]>>NC(=O)[C@@H]1CCCCC[C@@H]1N | COC(=O)[C@H]1[C@H](CCCCC1)N.[NH4+].[OH-].O>>N[C@@H]1[C@@H](CCCCC1)C(=O)N | CO[C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[NH2:11].[NH4+:1]>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[NH2:11] | COC(=O)[C@@H]1CCCCC[C@@H]1N.[NH4+] | NC(=O)[C@@H]1CCCCC[C@@H]1N | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | C1CCCCCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH4+;D0:6]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:6])=[O;D1;H0:2])-[C:5] | null | [] | null | null | 24 | HOUR | cis-2-Aminocycloheptanecarboxylic acid methyl ester (1.65 g, 9.64 mmol) was treated with 20 mL of NH4OH/H2O and stirred at room temperature for 24 h. The solution was concentrated in vacuo and azeotroped once with toluene. The reaction afforded 2.20 g of cis-2-aminocycloheptanecarboxylic acid amide as a white solid: 1H... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | C1CCCCCC1 | HO- | null | null | 24 | COC(=O)[C@@H]1CCCCC[C@@H]1N.[NH4+]>>NC(=O)[C@@H]1CCCCC[C@@H]1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b8b01e092bf4c23be15b02e57286005 | NC(=O)[C@H]1CCCC[C@H]1N.O=S(=O)(Cl)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | N[C@H]1[C@H](CCCC1)C(=O)N.ClC1=CC=C(C=C1)S(=O)(=O)Cl.C(C)N(CC)CC.Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@H](CCCC1)C(=O)N | [NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH2:10].Cl[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH:10][S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1 | NC(=O)[C@H]1CCCC[C@H]1N.O=S(=O)(Cl)c1ccc(Cl)cc1 | NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | null | null | ClCCl.CN(C)C=O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(NC1CCCCC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]-[C:11](-[N;D1;H2:12])=[O;D1;H0:13]>>[C:7]-[C:8](-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10]-[C:11](-[N;D1;H2:12])=[O;D1;H0:13] | 53.2 | [{"value": 53.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@H](CCCC1)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.2, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@H](CCCC1)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (1S,2R)-2-aminocyclohexanecarboxylic acid amide (16.2 mmol), 4-chlorobenzenesulfonylchloride (6.84 g, 32.4 mmol), and triethylamine (20 mL, 143 mmol) were stirred in dichloromethane/DMF (500 mL/100 mL) at room temperature for 6 h. The crude mixture was poured into 1 M hydrochloric acid (500 mL). The organi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | C1CCCCC1.c1ccccc1 | HCl | ClCCl.CN(C)C=O | null | null | NC(=O)[C@H]1CCCC[C@H]1N.O=S(=O)(Cl)c1ccc(Cl)cc1>ClCCl.CN(C)C=O>NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5401af972bfd4b98b671d0bcf01afd38 | NC(=O)[C@@H]1CCCC[C@@H]1N.O=S(=O)(Cl)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | N[C@@H]1[C@@H](CCCC1)C(=O)N.C(C)N(CC)CC.ClC1=CC=C(C=C1)S(=O)(=O)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N | [NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH2:10].Cl[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH:10][S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1 | NC(=O)[C@@H]1CCCC[C@@H]1N.O=S(=O)(Cl)c1ccc(Cl)cc1 | NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(NC1CCCCC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]-[C:11](-[N;D1;H2:12])=[O;D1;H0:13]>>[C:7]-[C:8](-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10]-[C:11](-[N;D1;H2:12])=[O;D1;H0:13] | 45.1 | [{"value": 45.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.1, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of cis-2-aminocyclohexanecarboxylic acid amide (2.0 g, 14.0 mmol), and triethylamine (3.9 mL, 28 mmol) in dichloromethane (100 mL) was added 4-chlorobenzenesulfonyl chloride (2.95 g, 14.0 mmol). The resulting solution was stirred at room temperature for 18 h. The reaction was then diluted with dichloromet... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | C1CCCCC1.c1ccccc1 | HCl | ClCCl | null | 18 | NC(=O)[C@@H]1CCCC[C@@H]1N.O=S(=O)(Cl)c1ccc(Cl)cc1>ClCCl>NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8edc0774097f4d56800f94b9e74b6e5c | NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@H](CCCC1)C(=O)O.ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N>>ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@H](CCCC1)C(=O)N | [NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH:10][S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH:10][S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1 | NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=S(=O)(NC1CCCCC1)c1ccccc1 | null | 96 | [{"value": 96.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@H](CCCC1)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (1S,2S)-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide was synthesized from (1S,2S)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid (0.76 mmol) according to the method described for the preparation of (1R,2S)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide. The crude pro... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCCCC1.c1ccccc1 | null | null | null | null | NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-92fc3ebc156c49bb94c274736e08c176 | COC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>O=C(O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | O.[OH-].[Li+].COC(=O)[C@H]1[C@H](CCCC1)NS(=O)(=O)C1=CC=C(C=C1)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)O | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH:10][S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH:10][S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1 | COC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | O=C(O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | null | null | CO.C1CCOC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=S(=O)(NC1CCCCC1)c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 80 | [{"value": 80.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Lithium hydroxide monohydrate (1.7 mmol) was added to a mixture of (1R,2S)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid methyl ester in THF (8 mL), methanol (8mL) and water (8 mL). Reaction stirred at room temperature overnight. Organic solvents were removed from the mixture in vacuo. Remaining aqueous w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCCC1.c1ccccc1 | Other | CO.C1CCOC1.O | null | 8 | COC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>CO.C1CCOC1.O>O=C(O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-961c80649e854235a82775b81e37070b | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@H](CCCC1)C(=O)N.BrCC1=CC=C(C(=O)OC)C=C1.C([O-])([O-])=O.[Cs+].[Cs+]>>COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCCC1)C(N)=O)=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:31][cH:30]1.[NH:10]([C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]1[C:17]([NH2:18])=[O:19])[S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([C@@H:11]2[CH2:12][CH... | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | COC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 22 | [{"value": 22.0, "product": "COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCCC1)C(N)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.6, "product": "COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCCC1)C(N)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of (1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (670 mg, 2.12 mmol), methyl 4-(bromomethyl)benzoate (534 mg, 2.33 mmol), cesium carbonate (1.04 g, 3.18 mmol) and acetonitrile (20 mL) was stirred vigorously at room temperature for 18 h. The crude mixture was filtered through celite... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HBr | C(C)#N | null | 18 | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>C(C)#N>COC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc3991aacb764debba28a8518c0c8a1b | CC(C)(C)c1ccc(CBr)cc1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>CC(C)(C)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@H](CCCC1)C(=O)N.BrCC1=CC=C(C=C1)C(C)(C)C>>C(C)(C)(C)C1=CC=C(CN([C@H]2[C@H](CCCC2)C(=O)N)S(=O)(=O)C2=CC=C(C=C2)Cl)C=C1 | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:31][cH:30]1.[NH:10]([C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]1[C:17]([NH2:18])=[O:19])[S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([C@@H:11]2[... | CC(C)(C)c1ccc(CBr)cc1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | CC(C)(C)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 69 | [{"value": 69.0, "product": "C(C)(C)(C)C1=CC=C(CN([C@H]2[C@H](CCCC2)C(=O)N)S(=O)(=O)C2=CC=C(C=C2)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound was prepared in 69% yield from (1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (75 mg, 0.237 mmol) and 1-bromomethyl-4-tert-butyl-benzene (57 mg, 0.249 mmol) according to the procedure described for Example 3: 1H NMR (500 Mz, DMSO) δ 7.58 (d, 2 H, J=8.9), 7.48 (d, 2 H, J=8.... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HBr | null | null | null | CC(C)(C)c1ccc(CBr)cc1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>CC(C)(C)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.