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-f64e217233764463aa5656221e71fb06 | CCOC(=O)c1c(C)cccc1OC.O=C1CCC(=O)N1Br>>CCOC(=O)c1c(CBr)cccc1OC | COC1=C(C(=O)OCC)C(=CC=C1)C.BrN1C(CCC1=O)=O>>BrCC1=CC=CC(=C1C(=O)OCC)OC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[cH:10][cH:11][cH:12][c:13]1[O:14][CH3:15].O=C1CCC(=O)N1[Br:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][Br:9])[cH:10][cH:11][cH:12][c:13]1[O:14][CH3:15] | CCOC(=O)c1c(C)cccc1OC.O=C1CCC(=O)N1Br | CCOC(=O)c1c(CBr)cccc1OC | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | C(Cl)(Cl)(Cl)Cl.C(C)OCC | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH2;D2;+0:7]-[Br;H0;D1;+0:1]):[c:8] | 60 | [{"value": 60.0, "product": "BrCC1=CC=CC(=C1C(=O)OCC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "BrCC1=CC=CC(=C1C(=O)OCC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of ethyl 2-methoxy-6-methylbenzoate (0.813 g, 4.19 mmol) in CCl4 (8 mL) was added recrystallized N-bromosuccinimide (0.751 g, 4.22 mmol) followed by benzoyl peroxide (52 mg, 0.22 mmol). The resultant mixture was heated to reflux for 90 minutes then cooled to room temperature. The mixture was diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl.C(C)OCC | null | null | CCOC(=O)c1c(C)cccc1OC.O=C1CCC(=O)N1Br>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl.C(C)OCC>CCOC(=O)c1c(CBr)cccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95b70511193241adae92e0a25d2fc02a | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.CCOC(=O)c1c(CBr)cccc1OC>>CCOC(=O)c1c(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cccc1OC | BrCC1=CC=CC(=C1C(=O)OCC)OC.C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21.C(C)(C)N(C(C)C)CC>>C(C)OC(C1=C(C=CC=C1OC)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O | CC(C)(C)OC(=O)[n:19]1[c:11]([CH2:10][NH:9][CH:20]2[CH2:21][CH2:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][n:28][c:29]32)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21.Br[CH2:8][c:7]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:33]([O:34][CH3:35])[cH:32][cH:31][cH:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][N... | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.CCOC(=O)c1c(CBr)cccc1OC | CCOC(=O)c1c(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cccc1OC | null | null | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | 17108821a068f98f079601c47c81a405dc4c6cd269aa21d9ab86da2340878e46 | dcef1ea55ad1210a12e0b130cb0ce884a6e70a93af8e5e171bad3167757624df | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:8]1:[c:9](-[C:10]-[NH;D2;+0:11]-[C:12](-[C:13])-[c:14]:[#7;a:15]):[#7;a:16]:[c:17](:[c:18]):[c:19]:1:[c:20]>>[#7;a:15]:[c:14]-[C:12](-[N;H0;D3;+0:11](-[C:10]-[c:9]1:[#7;a:16]:[c:17](:[c:18]):[c:19](:[c:20]):[nH;D2;+0:8]:1)-[... | 74.8 | [{"value": 62.0, "product": "C(C)OC(C1=C(C=CC=C1OC)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.8, "product": "C(C)OC(C1=C(C=CC=C1OC)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.409 g, 1.08 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.38 mL, 2.18 mmol) followed by a solution of ethyl 6-(bromomethyl)-2-methoxybenzoate (0.454 g, 1.66 mmol) in CH3CN (6 mL). The resultant... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Secondary amine.Boc | Tertiary amine | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HBr | CC#N | null | null | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.CCOC(=O)c1c(CBr)cccc1OC>CC#N>CCOC(=O)c1c(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f9221e72fbe144d09bdbb0a053ea0eea | CCO.Nc1ccc(C(=O)O)cn1>>CCOC(=O)c1ccc(N)nc1 | NC1=NC=C(C(=O)O)C=C1.CCO>>C(C)OC(C1=CN=C(C=C1)N)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[n:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[n:11][cH:12]1 | CCO.Nc1ccc(C(=O)O)cn1 | CCOC(=O)c1ccc(N)nc1 | null | null | S(O)(O)(=O)=O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C;D1;H3:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 92 | [{"value": 92.0, "product": "C(C)OC(C1=CN=C(C=C1)N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-aminonicotinic acid (2.0 g, 14.4 mmol) in anhydrous EtOH (70 mL) and concentrated sulfuric acid (14 mL) was heated to reflux for 16 h. The solution was concentrated under reduced pressure, neutralized with saturated aqueous Na2CO3 (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic phases ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccncc1 | HO- | S(O)(O)(=O)=O | null | null | CCO.Nc1ccc(C(=O)O)cn1>S(O)(O)(=O)=O>CCOC(=O)c1ccc(N)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d190122b5b7460ba966849f68654cfe | CCOC(=O)c1ccc(N)nc1>>Nc1ccc(CO)cn1 | C(C)OC(C1=CN=C(C=C1)N)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>NC1=CC=C(C=N1)CO | CCO[C:6]([c:5]1[cH:4][cH:3][c:2]([NH2:1])[n:9][cH:8]1)=[O:7]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][OH:7])[cH:8][n:9]1 | CCOC(=O)c1ccc(N)nc1 | Nc1ccc(CO)cn1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 69.2 | [{"value": 69.0, "product": "NC1=CC=C(C=N1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.2, "product": "NC1=CC=C(C=N1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 6-aminonicotinic acid ethyl ester (1.18 g, 7.1 mmol) in anhydrous THF (24 mL) was added a solution of lithium aluminum hydride (0.41 g, 10.6 mmol) in THF (12 mL) at 0° C. over 10 min and the mixture stirred for 1.5 h. To the reaction was added sequentially 0.5 mL H2O, 0.5 mL 15% aqueous NaOH and 1.5 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 1.5 | CCOC(=O)c1ccc(N)nc1>C1CCOC1>Nc1ccc(CO)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4cc2c5bab2ba4ae7a526bb2725f4a01a | CCO.Nc1ncccc1C(=O)O>>CCOC(=O)c1cccnc1N | NC1=C(C(=O)O)C=CC=N1.CCO>>C(C)OC(C1=C(N=CC=C1)N)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1[NH2:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1[NH2:12] | CCO.Nc1ncccc1C(=O)O | CCOC(=O)c1cccnc1N | null | null | S(O)(O)(=O)=O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[N;D1;H2:6]):[#7;a:7]:[c:8].[C;D1;H3:9]-[C:10]-[OH;D1;+0:11]>>[C;D1;H3:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[N;D1;H2:6]):[#7;a:7]:[c:8] | 74 | [{"value": 74.0, "product": "C(C)OC(C1=C(N=CC=C1)N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-aminonicotinic acid (2.0 g, 14.4 mmol) in anhydrous EtOH (70 mL) and concentrated sulfuric acid (14 mL) was heated to reflux for 16 h. The solution was concentrated under reduced pressure, neutralized with saturated aqueous Na2CO3 (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic phases ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccncc1 | HO- | S(O)(O)(=O)=O | null | null | CCO.Nc1ncccc1C(=O)O>S(O)(O)(=O)=O>CCOC(=O)c1cccnc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-075f816db41f43d982f69b4ea63db836 | CCOC(=O)c1cccnc1N>>Nc1ncccc1CO | C(C)OC(C1=C(N=CC=C1)N)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>NC1=NC=CC=C1CO | CCO[C:8]([c:7]1[c:2]([NH2:1])[n:3][cH:4][cH:5][cH:6]1)=[O:9]>>[NH2:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][OH:9] | CCOC(=O)c1cccnc1N | Nc1ncccc1CO | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[N;D1;H2:6]):[#7;a:7]:[c:8]>>[N;D1;H2:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | 79 | [{"value": 79.0, "product": "NC1=NC=CC=C1CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.0, "product": "NC1=NC=CC=C1CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 2-aminonicotinic acid ethyl ester (1.74 g, 10.5 mmol) in anhydrous THF (35 mL) was added a solution of lithium aluminum hydride (0.60 g, 15.7 mmol) in THF (17 mL) at 0° C. over 15 min and the mixture stirred for 1.5 h. To the reaction was added sequentially 0.6 mL H2O, 0.6 mL 15% aqueous NaOH and 1.8 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 1.5 | CCOC(=O)c1cccnc1N>C1CCOC1>Nc1ncccc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5586f7ec09c7462e83e5bffdfa46fd2c | CC(C)(C)OC(=O)NC(=Nc1ccc(CO)cc1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)NC(=Nc1ccc(C=O)cc1)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NC(=NC1=CC=C(C=C1)CO)NC(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)NC(=NC1=CC=C(C=C1)C=O)NC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9](=[N:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][OH:16])[cH:17][cH:18]1)[NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9](=[N:10][c:11]1[cH:12][cH:13][c:14]([CH:15]=[O:16])[cH:17][cH:18]1)[NH... | CC(C)(C)OC(=O)NC(=Nc1ccc(CO)cc1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)NC(=Nc1ccc(C=O)cc1)NC(=O)OC(C)(C)C | null | O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 93 | [{"value": 93.0, "product": "C(C)(C)(C)OC(=O)NC(=NC1=CC=C(C=C1)C=O)NC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "C(C)(C)(C)OC(=O)NC(=NC1=CC=C(C=C1)C=O)NC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The alcohol (0.282 g, 0.771 mmol) from above was dissolved in CH2Cl2 (7 mL), treated with activated MnO2 (0.696 g, 8.01 mmol) and stirred at room temperature overnight. The mixture was filtered through celite® and the cake was washed with CH2Cl2. The solvent was removed from the filtrate under reduced pressure and prov... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | O=[Mn]=O.C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)NC(=Nc1ccc(CO)cc1)NC(=O)OC(C)(C)C>O=[Mn]=O.C(Cl)Cl>CC(C)(C)OC(=O)NC(=Nc1ccc(C=O)cc1)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06ce467704a54a0da0b610410266fe46 | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.OO>>ON=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | N1C(=NC2=C1C=CC=C2)CN(CC2=CC=C(C=C2)CN)C2CCCC=1C=CC=NC21.OO.C([O-])(O)=O.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=NO)C=C2 | [NH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([CH2:10][c:11]2[n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[nH:19]2)[CH:20]2[CH2:21][CH2:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][n:28][c:29]32)[cH:30][cH:31]1.O[OH:1]>>[OH:1][N:2]=[CH:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([CH2:10][c:11]2[n:12][c:13]3[cH:14][cH:15]... | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.OO | ON=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | O.O.[O-][W](=O)(=O)[O-].[Na+].[Na+] | CO | Protection | OtherReaction | ccd8db1a5ad0bccce83a917ba35a768e51fd9b0f0fdba8dbf0ea738878cdb76f | 68c9fb0d27941f317687f34c279aad1cd59d8a4998653330d6a3e417d9ebc750 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | O-[OH;D1;+0:1].[NH2;D1;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[OH;D1;+0:1]-[N;H0;D2;+0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6] | 63 | [{"value": 63.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C=NO)C=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.50 mmol) in MeOH (5 mL) was added solid sodium tungstate dihydrate (332 mg, 1.0 mmol) followed by a 35 wt % aqueous solution of hydrogen peroxide (2.9 mL, 30 mmol). The resulting suspension ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Peroxide | Oxime | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HO- | O.O.[O-][W](=O)(=O)[O-].[Na+].[Na+].CO | null | 3 | NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.OO>O.O.[O-][W](=O)(=O)[O-].[Na+].[Na+].CO>ON=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4dd51a94b3f84cc8af5bb71648f4d623 | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.COC(=O)c1ccc(C=O)cc1>>COC(=O)c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C([O-])(O)=O.[Na+].C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21.C(=O)C1=CC=C(C(=O)OC)C=C1.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>COC(C1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O | CC(C)(C)OC(=O)[n:20]1[c:12]([CH2:11][NH:10][CH:21]2[CH2:22][CH2:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][n:29][c:30]32)[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21.O=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:32][cH:31]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([CH2:11][c:12]... | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.COC(=O)c1ccc(C=O)cc1 | COC(=O)c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | C(=O)(C(F)(F)F)O.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 5c0c8b7531ec7bf342267fceb03bccfc403ce7adf26771d35132e015e0725d40 | d2dd3f846392ce974ba3615cb24bcfba6aac78fab3fe5b5cd0e60a3c903fcd55 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[C:3]-[NH;D2;+0:4]-[C:5](-[C:6])-[c:7]:[#7;a:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13].O=[CH;D2;+0:14]-[c:15](:[c:16]):[c:17]>>[#7;a:8]:[c:7]-[C:5](-[N;H0;D3;+0:4](-[C:3]-[c:2]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:1]:1)-[CH2;D2;+0:14]-[c:15](:[c:16]):[c:17])-... | 74 | [{"value": 74.0, "product": "COC(C1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.6, "product": "COC(C1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Following General Procedure B: To a solution of (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (680 mg, 1.8 mmol) and methyl 4-formylbenzoate (295 mg, 1.8 mmol) in CH2Cl2 (10 mL) was added NaBH(OAc)3 (763 mg, 3.6 mmol) and the mixture stirred for 18 h. The resulting crude ma... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Secondary amine.Boc | Tertiary amine | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HO- | C(=O)(C(F)(F)F)O.C(Cl)Cl | null | 18 | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.COC(=O)c1ccc(C=O)cc1>C(=O)(C(F)(F)F)O.C(Cl)Cl>COC(=O)c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b74f5706fcb7405d87133dc30ae3f25c | COC(=O)c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.NN>>NNC(=O)c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C([O-])(O)=O.[Na+].COC(C1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC=C2)=O.O.NN>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C(=O)NN)C=C2 | CO[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([CH2:11][c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[nH:20]2)[CH:21]2[CH2:22][CH2:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][n:29][c:30]32)[cH:31][cH:32]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([CH2:11][c:12]2[n:13][c:... | COC(=O)c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.NN | NNC(=O)c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | null | null | C(C)O | Acylation | Aminolysis of esters | 2e40a14c7d71c6b9001f460fbb953805c923b2db988c8c04f234b9bb5f04424f | 3b636feb164ef0f3c8a4f1764f18a25b9eee32ed1463e3bb4b6f1becb871ca74 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[NH2;D1;+0:7]>>[N;D1;H2:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 63.2 | [{"value": 61.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C(=O)NN)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.2, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=C(C(=O)NN)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a stirred solution of 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzoic acid methyl ester (AMD9711) (140 mg, 0.33 mmol) in dry ethanol (3 mL) was added hydrazine monohydrate (0.5 mL, 10.3 mmol) and the resulting mixture was heated at 80° C. for 24 h. Saturated aqueous sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester | Acylhydrazine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HO- | C(C)O | 80 | null | COC(=O)c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1.NN>C(C)O>NNC(=O)c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-08381d0f80044bf994b13f6803c6eb40 | BrCc1ccccc1CBr.O=C1c2ccccc2C(=O)N1O>>O=C1c2ccccc2C(=O)N1OCc1ccccc1CBr | ON1C(C=2C(C1=O)=CC=CC2)=O.CCN(CC)CC.BrCC=1C(=CC=CC1)CBr>>BrCC1=C(CON2C(C3=CC=CC=C3C2=O)=O)C=CC=C1 | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[CH2:20][Br:21].[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[OH:12]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[CH2:20][Br:21] | BrCc1ccccc1CBr.O=C1c2ccccc2C(=O)N1O | O=C1c2ccccc2C(=O)N1OCc1ccccc1CBr | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | fa354e521a6eba522f3edb5b01d9a1a9ef9e52105a2e891a13a467f695a0cabb | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C1c2ccccc2C(=O)N1OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[c:7]:[c:8]-[C:9](=[O;D1;H0:10])-[#7:11]-1-[OH;D1;+0:12]>>[O;D1;H0:5]=[C:6]1-[c:7]:[c:8]-[C:9](=[O;D1;H0:10])-[#7:11]-1-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 46 | [{"value": 46.0, "product": "BrCC1=C(CON2C(C3=CC=CC=C3C2=O)=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.6, "product": "BrCC1=C(CON2C(C3=CC=CC=C3C2=O)=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a stirred solution of N-hydroxyphthalimide (0.60 g, 3.68 mmol) and Et3N (0.60 mL, 4.30 mmol) in DMF (6 mL) was added α,α′-dibromo-o-xylene (3.30 g, 0.0125 mol) and the mixture stirred at room temperature for 4 h. The resultant brown precipitate was filtered and washed with CH2Cl2. The filtrate was diluted with EtOAc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HBr | CN(C)C=O | null | 4 | BrCc1ccccc1CBr.O=C1c2ccccc2C(=O)N1O>CN(C)C=O>O=C1c2ccccc2C(=O)N1OCc1ccccc1CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b31324e4f2c4d8182cec42303622a5d | CO.Cc1ccc([N+](=O)[O-])cc1C(=O)O>>COC(=O)c1cc([N+](=O)[O-])ccc1C | CC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].OS(=O)(=O)O.CO>>COC(C1=C(C=CC(=C1)[N+](=O)[O-])C)=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[CH3:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[CH3:14] | CO.Cc1ccc([N+](=O)[O-])cc1C(=O)O | COC(=O)c1cc([N+](=O)[O-])ccc1C | 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;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 73 | [{"value": 73.0, "product": "COC(C1=C(C=CC(=C1)[N+](=O)[O-])C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-methyl-5-nitrobenzoic acid (1.91 g, 10.6 mmol) and H2SO4 (catalytic) in MeOH (25 mL) was heated at reflux for 16 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (50 mL), washed with saturated NaHCO3(aq) (2×40 mL), then dried (MgSO4), filtered, and concentrated in vacuo to give yellow ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.Cc1ccc([N+](=O)[O-])cc1C(=O)O>>COC(=O)c1cc([N+](=O)[O-])ccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f389573b6e7429ebe8c788e377a0f58 | COC(=O)c1cc([N+](=O)[O-])ccc1C>>COC(=O)c1cc(N)ccc1C | COC(C1=C(C=CC(=C1)[N+](=O)[O-])C)=O>>COC(C1=C(C=CC(=C1)N)C)=O | O=[N+:8]([O-])[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([CH3:12])[cH:10][cH:9]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[CH3:12] | COC(=O)c1cc([N+](=O)[O-])ccc1C | COC(=O)c1cc(N)ccc1C | null | [Pd] | CO.CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100.1 | [{"value": 99.0, "product": "COC(C1=C(C=CC(=C1)N)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.1, "product": "COC(C1=C(C=CC(=C1)N)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-methyl-5-nitro-benzoic acid methyl ester (1.50 g, 7.8 mmol) in 4:1 MeOH/EtOAc (20 mL) was shaken at room temperature with a suspension of 10% Pd/C (175 mg, 0.17 mmol) under hydrogen atmosphere (35 psi) for 17 h. The catalyst was removed by filtration over celite, and the filtrate was concentrated in vac... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO.CCOC(=O)C | null | null | COC(=O)c1cc([N+](=O)[O-])ccc1C>[Pd].CO.CCOC(=O)C>COC(=O)c1cc(N)ccc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8c191f4c49e4165b58ee9f2d4333e3c | COC(=O)c1ccc(CN(Cc2nc3ccccc3n2C(=O)OC(C)(C)C)C2CCCc3cccnc32)c(C#N)c1.N>>N#Cc1cc(C(N)=O)ccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 | C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=C(C=C(C=C2)C(=O)OC)C#N.N>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=C(C=C(C(=O)N)C=C2)C#N | CO[C:6]([c:5]1[cH:4][c:3]([C:2]#[N:1])[c:11]([CH2:12][N:13]([CH2:14][c:15]2[n:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[n:23]2C(=O)OC(C)(C)C)[CH:24]2[CH2:25][CH2:26][CH2:27][c:28]3[cH:29][cH:30][cH:31][n:32][c:33]32)[cH:10][cH:9]1)=[O:8].[NH3:7]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([C:6]([NH2:7])=[O:8])[cH:9][cH:10][c:11]... | COC(=O)c1ccc(CN(Cc2nc3ccccc3n2C(=O)OC(C)(C)C)C2CCCc3cccnc32)c(C#N)c1.N | N#Cc1cc(C(N)=O)ccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 | null | [Ni] | CO.O | Acylation | OtherReaction | 8734052336d673834f39e3cc99dac0bedd77895b0ce8dcd42c11ec87e36de3ca | 19a46495b8fd554d1d9b4ad933b2fc9889f00f8e1236eaec1dd32afb08efa229 | c1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[C:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].C-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13].[NH3;D0;+0:14]>>[C:3]-[c:2]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[nH;D2;+0:1]:1.[NH2;D1;+0:14]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13] | 36 | [{"value": 36.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=C(C=C(C(=O)N)C=C2)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To 0.5 mL of Raney Nickel in water was added a solution of 2-{[(2-cyano-4-methoxycarbonyl-benzyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-methyl}-benzimidazole-1-carboxylic acid tert-butyl ester (0.55 g, 1 mmol) in methanol (25 mL). The solution was then saturated with ammonia gas for 10 minutes. The reaction vessel w... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Boc | Primary amide | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2 | HO- | [Ni].CO.O | null | 16 | COC(=O)c1ccc(CN(Cc2nc3ccccc3n2C(=O)OC(C)(C)C)C2CCCc3cccnc32)c(C#N)c1.N>[Ni].CO.O>N#Cc1cc(C(N)=O)ccc1CN(Cc1nc2ccccc2[nH]1)C1CCCc2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a8bb6473bd14813a5e1baaa37696a7d | Cc1ccc2ocnc2c1.O=C1CCC(=O)N1Br>>BrCc1ccc2ocnc2c1 | CC=1C=CC2=C(N=CO2)C1.BrN1C(CCC1=O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C>>BrCC=1C=CC2=C(N=CO2)C1 | [CH3:2][c:3]1[cH:4][cH:5][c:6]2[o:7][cH:8][n:9][c:10]2[cH:11]1.O=C1CCC(=O)N1[Br:1]>>[Br:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[o:7][cH:8][n:9][c:10]2[cH:11]1 | Cc1ccc2ocnc2c1.O=C1CCC(=O)N1Br | BrCc1ccc2ocnc2c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc2ocnc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[c:3]:[c:4]:[c:5](-[CH3;D1;+0:6]):[c:7]>>[#7;a:2]:[c:3]:[c:4]:[c:5](-[CH2;D2;+0:6]-[Br;H0;D1;+0:1]):[c:7] | 39.6 | [{"value": 39.0, "product": "BrCC=1C=CC2=C(N=CO2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.6, "product": "BrCC=1C=CC2=C(N=CO2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-methylbenzoxazole (200 mg, 1.50 mmol), N-bromosuccinimide (321 mg, 1.80 mmol), and 2,2′-azobisisobutyronitrile (37 mg, 0.23 mmol) in CCl4 (3 mL) was heated at reflux for 22 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the crude material on silica g... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc2ocnc2c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>BrCc1ccc2ocnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e3cc0077e4c14e81be0b4dc412ae5316 | Cc1ccc2ncoc2c1.O=C1CCC(=O)N1Br>>BrCc1ccc2ncoc2c1 | CC1=CC2=C(N=CO2)C=C1.BrN1C(CCC1=O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C>>BrCC1=CC2=C(N=CO2)C=C1 | [CH3:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][o:9][c:10]2[cH:11]1.O=C1CCC(=O)N1[Br:1]>>[Br:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][o:9][c:10]2[cH:11]1 | Cc1ccc2ncoc2c1.O=C1CCC(=O)N1Br | BrCc1ccc2ncoc2c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc2ocnc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8;a:2]:[c:3]:[c:4]:[c:5](-[CH3;D1;+0:6]):[c:7]>>[#8;a:2]:[c:3]:[c:4]:[c:5](-[CH2;D2;+0:6]-[Br;H0;D1;+0:1]):[c:7] | 38.2 | [{"value": 38.0, "product": "BrCC1=CC2=C(N=CO2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.2, "product": "BrCC1=CC2=C(N=CO2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-methylbenzoxazole (422 mg, 3.17 mmol), N-bromosuccinimide (677 mg, 3.80 mmol), and 2,2′-azobisisobutyronitrile (78 mg, 0.48 mmol) in CCl4 (6.3 mL) was heated at reflux for 22 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the crude material on silica... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccc2ocnc2c1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc2ncoc2c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>BrCc1ccc2ncoc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf56584023f540c7948984614ab8fea3 | Cc1cccc(N)c1N>>Cc1cccc2[nH]cnc12 | NC1=C(C=CC=C1N)C.COC(OC)OC.FC(C(=O)O)(F)F>>CC1=CC=CC=2NC=NC21 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[c:10]1[NH2:9]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][cH:8][n:9][c:10]12 | Cc1cccc(N)c1N | Cc1cccc2[nH]cnc12 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 66f368bbbaf19caaae899f978490a7d3489a30ef27df09744dd58c54a4878758 | f6ca1788fc80057bd663c067fa50bcd2911a68a96991f331ace1350d4975ef8f | c1ccc2[nH]cnc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6]>>[c:6]:[c:4]1:[n;H0;D2;+0:5]:[c:7]:[nH;D2;+0:1]:[c:2]:1:[c:3] | null | [] | null | null | 24 | HOUR | To a stirred solution of 2,3-diaminotoluene (1.00 g, 8.2 mmol) in CH2Cl2 (82 mL) was added trimethylorthoformate (4.5 mL, 41 mmol) and trifluoroacetic acid (0.32 mL, 4.1 mmol) and the mixture stirred at room temperature for 24 h after which the reaction mixture was diluted with CH2Cl2 (200 mL), and washed consecutively... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | Other | C(Cl)Cl | null | 24 | Cc1cccc(N)c1N>C(Cl)Cl>Cc1cccc2[nH]cnc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dab199994697470a9010da92e0d118eb | Cc1cccc2c1ncn2C(=O)OC(C)(C)C.O=C1CCC(=O)N1Br>>CC(C)(C)OC(=O)n1cnc2c(CBr)cccc21 | C(C)(C)(C)OC(=O)N1C=NC2=C1C=CC=C2C.BrN1C(CCC1=O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C>>C(C)(C)(C)OC(=O)N1C=NC2=C1C=CC=C2CBr | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][n:10][c:11]2[c:12]([CH3:13])[cH:15][cH:16][cH:17][c:18]12.O=C1CCC(=O)N1[Br:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][n:10][c:11]2[c:12]([CH2:13][Br:14])[cH:15][cH:16][cH:17][c:18]12 | Cc1cccc2c1ncn2C(=O)OC(C)(C)C.O=C1CCC(=O)N1Br | CC(C)(C)OC(=O)n1cnc2c(CBr)cccc21 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc2[nH]cnc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1 | 60 | [{"value": 60.0, "product": "C(C)(C)(C)OC(=O)N1C=NC2=C1C=CC=C2CBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "C(C)(C)(C)OC(=O)N1C=NC2=C1C=CC=C2CBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 4-methyl-benzimidazole-1-carboxylic acid tert-butyl ester (800 mg, 3.4 mmol) in CCl4 (7 mL) was added N-bromosuccinimide (730 mg, 4.1 mmol) and 2,2′-azobis(2-methylpropionitrile) (84 mg, 0.51 mmol). The resultant mixture was heated at reflux for 18 h after which it was filtered and concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1cccc2[nH]cnc12 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1cccc2c1ncn2C(=O)OC(C)(C)C.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>CC(C)(C)OC(=O)n1cnc2c(CBr)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a73ae5db738043a19c06fc8e82d6e4e3 | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1ccncc1>>c1cnc2c(c1)CCCC2N(Cc1ccncc1)Cc1nc2ccccc2[nH]1 | C([O-])(O)=O.[Na+].C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21.N1=CC=C(C=C1)C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=NC=C2 | CC(C)(C)OC(=O)[n:28]1[c:20]([CH2:19][NH:11][CH:10]2[c:4]3[n:3][cH:2][cH:1][cH:6][c:5]3[CH2:7][CH2:8][CH2:9]2)[n:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21.O=[CH:12][c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:13]1[cH:14][cH:15][n:16... | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1ccncc1 | c1cnc2c(c1)CCCC2N(Cc1ccncc1)Cc1nc2ccccc2[nH]1 | null | null | C(=O)(C(F)(F)F)O.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 5c0c8b7531ec7bf342267fceb03bccfc403ce7adf26771d35132e015e0725d40 | d2dd3f846392ce974ba3615cb24bcfba6aac78fab3fe5b5cd0e60a3c903fcd55 | c1cnc2c(c1)CCCC2N(Cc1ccncc1)Cc1nc2ccccc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[C:3]-[NH;D2;+0:4]-[C:5](-[C:6])-[c:7]:[#7;a:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13].O=[CH;D2;+0:14]-[c:15]1:[c:16]:[c:17]:[#7;a:18]:[c:19]:[c:20]:1>>[#7;a:8]:[c:7]-[C:5](-[N;H0;D3;+0:4](-[C:3]-[c:2]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:1]:1)-[CH2;D2;+0:14]... | 70.2 | [{"value": 70.0, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=NC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.2, "product": "N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=NC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Following General Procedure B: To a solution of (1-tert-butoxycarbonyl-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amine (120 mg, 0.32 mmol) and 4-pyridinecarboxaldehyde (30 μL, 0.32 mmol) in CH2Cl2 (5 mL) was added sodium triacetoxyborohydride (136 mg, 0.64 mmol) and the reaction stirred for 18 h. The r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Secondary amine.Boc | Tertiary amine | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1cnc2c(c1)CCCC2.c1ccncc1.c1ccc2[nH]cnc2c1 | HO- | C(=O)(C(F)(F)F)O.C(Cl)Cl | null | 18 | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1ccncc1>C(=O)(C(F)(F)F)O.C(Cl)Cl>c1cnc2c(c1)CCCC2N(Cc1ccncc1)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d456dfb703e64667b6df6014cffdddf0 | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1ccc2c(c1)OCO2>>c1cnc2c(c1)CCCC2N(Cc1ccc2c(c1)OCO2)Cc1nc2ccccc2[nH]1 | C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21.C1=CC2=C(C=C1C=O)OCO2.CC(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>O1COC2=C1C=CC(=C2)CN(C2CCCC=1C=CC=NC21)CC2=NC1=C(N2)C=CC=C1 | CC(C)(C)OC(=O)[n:31]1[c:23]([CH2:22][NH:11][CH:10]2[c:4]3[n:3][cH:2][cH:1][cH:6][c:5]3[CH2:7][CH2:8][CH2:9]2)[n:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]21.O=[CH:12][c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[O:19][CH2:20][O:21]2>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:... | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1ccc2c(c1)OCO2 | c1cnc2c(c1)CCCC2N(Cc1ccc2c(c1)OCO2)Cc1nc2ccccc2[nH]1 | null | null | C1CCOC1.FC(C(=O)O)(F)F.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 5c0c8b7531ec7bf342267fceb03bccfc403ce7adf26771d35132e015e0725d40 | d2dd3f846392ce974ba3615cb24bcfba6aac78fab3fe5b5cd0e60a3c903fcd55 | c1cnc2c(c1)CCCC2N(Cc1ccc2c(c1)OCO2)Cc1nc2ccccc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[C:3]-[NH;D2;+0:4]-[C:5](-[C:6])-[c:7]:[#7;a:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13].O=[CH;D2;+0:14]-[c:15](:[c:16]):[c:17]>>[#7;a:8]:[c:7]-[C:5](-[N;H0;D3;+0:4](-[C:3]-[c:2]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:1]:1)-[CH2;D2;+0:14]-[c:15](:[c:16]):[c:17])-... | 33.1 | [{"value": 33.0, "product": "O1COC2=C1C=CC(=C2)CN(C2CCCC=1C=CC=NC21)CC2=NC1=C(N2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.1, "product": "O1COC2=C1C=CC(=C2)CN(C2CCCC=1C=CC=NC21)CC2=NC1=C(N2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Using General Procedure B: To a solution of [1-(tert-butoxycarbonyl)-(1H-benzimidazol-2-ylmethyl)]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (125 mg, 0.33 mmol), piperonal (50 mg, 0.33 mmol) and AcOH (0.02 mL, 0.33 mmol) in THF (3.3 mL) was added NaBH(OAc)3 (210 mg, 0.99 mmol) and the resultant suspension stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Secondary amine.Boc | Tertiary amine | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1cnc2c(c1)CCCC2.c1ccc2c(c1)OCO2.c1ccc2[nH]cnc2c1 | HO- | C1CCOC1.FC(C(=O)O)(F)F.C(Cl)Cl | null | 1.5 | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1ccc2c(c1)OCO2>C1CCOC1.FC(C(=O)O)(F)F.C(Cl)Cl>c1cnc2c(c1)CCCC2N(Cc1ccc2c(c1)OCO2)Cc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff392881b94248d4b1fd278693bd58ef | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1cccc2c1OCC2>>c1cnc2c(c1)CCCC2N(Cc1nc2ccccc2[nH]1)Cc1cccc2c1OCC2 | O1CCC2=C1C(=CC=C2)C=O.C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>N1C(=NC2=C1C=CC=C2)CN(C2CCCC=1C=CC=NC21)CC2=CC=CC=1CCOC12 | CC(C)(C)OC(=O)[n:21]1[c:13]([CH2:12][NH:11][CH:10]2[c:4]3[n:3][cH:2][cH:1][cH:6][c:5]3[CH2:7][CH2:8][CH2:9]2)[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21.O=[CH:22][c:23]1[cH:24][cH:25][cH:26][c:27]2[c:28]1[O:29][CH2:30][CH2:31]2>>[cH:1]1[cH:2][n:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH2:9][CH:10]2[N:11]([CH2:12][c:... | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1cccc2c1OCC2 | c1cnc2c(c1)CCCC2N(Cc1nc2ccccc2[nH]1)Cc1cccc2c1OCC2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5c0c8b7531ec7bf342267fceb03bccfc403ce7adf26771d35132e015e0725d40 | d2dd3f846392ce974ba3615cb24bcfba6aac78fab3fe5b5cd0e60a3c903fcd55 | c1cnc2c(c1)CCCC2N(Cc1nc2ccccc2[nH]1)Cc1cccc2c1OCC2 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[C:3]-[NH;D2;+0:4]-[C:5](-[C:6])-[c:7]:[#7;a:8]):[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13].O=[CH;D2;+0:14]-[c:15](:[c:16]):[c:17]-[#8:18]>>[#7;a:8]:[c:7]-[C:5](-[N;H0;D3;+0:4](-[C:3]-[c:2]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:1]:1)-[CH2;D2;+0:14]-[c:15](:[c:16]):... | null | [] | null | null | 8 | HOUR | Following General Procedure B: To a solution of 2,3-dihydrobenzofuran-7-carboxaldehyde (53.6 mg, 0.362 mmol) and [1-(tert-butoxycarbonyl)-(1H-benzimidazol-2-ylmethyl)]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (136 mg, 0.361 mmol) CH2Cl2 (5 mL) was added NaBH(OAc)3 (112 mg, 0.528 mmol) and the mixture stirred overnight.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Secondary amine.Boc | Tertiary amine | c1nc2ccccc2[nH]1 | c1ccc2[nH]cnc2c1 | c1cnc2c(c1)CCCC2.c1ccc2[nH]cnc2c1.c1ccc2c(c1)CCO2 | HO- | null | null | 8 | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1cccc2c1OCC2>>c1cnc2c(c1)CCCC2N(Cc1nc2ccccc2[nH]1)Cc1cccc2c1OCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b9008a354c184d54bf57d34ec3e39e40 | O=C(O)c1ccc2nc[nH]c2c1>>O=Cc1ccc2[nH]cnc2c1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].N1=CNC2=C1C=CC(=C2)C(=O)O>>N1C=NC2=C1C=CC(=C2)C=O | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][nH:9][c:10]2[cH:11]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][n:9][c:10]2[cH:11]1 | O=C(O)c1ccc2nc[nH]c2c1 | O=Cc1ccc2[nH]cnc2c1 | null | [O-2].[Mn+4].[O-2] | CO.C1CCOC1.C(Cl)Cl | Reduction | OtherReaction | 78999da0d33b2c10ff8c3d41626c41ea14d2697ff6d1d7e5baf78453ec38592a | f41d7c101137b93550fdf296ceb4547d1ce640e4cbceb5b7b006723d153456c9 | c1ccc2[nH]cnc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]2:[nH;D2;+0:6]:[c:7]:[n;H0;D2;+0:8]:[c:9]:2:[c:10]:[c:11]:1>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3]1:[c:4]:[c:5]2:[n;H0;D2;+0:6]:[c:7]:[nH;D2;+0:8]:[c:9]:2:[c:10]:[c:11]:1 | 60 | [{"value": 60.0, "product": "N1C=NC2=C1C=CC(=C2)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.9, "product": "N1C=NC2=C1C=CC(=C2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | LiAlH4 (1.0 m in THF, 10 mL, 10 mmol) was added dropwise to a suspension of 5-benzimidazolecarboxylic acid (500 mg, 3.08 mmol) in THF (20 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 24 h followed by heating at 50° C. for an addition 24 h. MeOH (4×5 mL) was added and the solution was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aldehyde | null | null | c1ccc2[nH]cnc2c1 | Other | [O-2].[Mn+4].[O-2].CO.C1CCOC1.C(Cl)Cl | null | 24 | O=C(O)c1ccc2nc[nH]c2c1>[O-2].[Mn+4].[O-2].CO.C1CCOC1.C(Cl)Cl>O=Cc1ccc2[nH]cnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51d8cffd0bfc4c71b60b3e003da859bb | COC(=O)c1ccc(C(=O)Cl)cc1.Nc1ccccc1[N+](=O)[O-]>>COC(=O)c1ccc(C(N)=O)cc1-c1ccccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(N)C=CC=C1.COC(=O)C1=CC=C(C=C1)C(=O)Cl.N1=CC=CC=C1>>COC(C1=C(C=C(C(=O)N)C=C1)C1=C(C=CC=C1)[N+](=O)[O-])=O | Cl[C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13][cH:12]1)=[O:11].[NH2:10][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[N+:20](=[O:21])[O-:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH2:10])=[O:11])[cH:12][c:13]1-[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[N+:20](=[O:21])[O-:22] | COC(=O)c1ccc(C(=O)Cl)cc1.Nc1ccccc1[N+](=O)[O-] | COC(=O)c1ccc(C(N)=O)cc1-c1ccccc1[N+](=O)[O-] | null | null | C([O-])(O)=O.[Na+].CCOC(=O)C.C1CCOC1 | Acylation | OtherReaction | 12dd3f819dff59afa8891afe5b791765929088d08a6a860b329b54d142454e01 | 5d86061e72bfd6a9511ca0dd8b67e7f96dd93b070d7199a24f9e8328c94bd93b | c1ccc(-c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[cH;D2;+0:5]:[c:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]):[c:11]:[c:12]:1.[#7;+:13]-[c:14](:[c:15]):[c;H0;D3;+0:16](-[NH2;D1;+0:17]):[c:18]:[c:19]>>[#7;+:13]-[c:14](:[c:15]):[c;H0;D3;+0:16](-[c;H0;D3;+0:5]1:[c:4]:[c:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:17])=[O;D1;H0:2]):[c:12]:... | 78 | [{"value": 78.0, "product": "COC(C1=C(C=C(C(=O)N)C=C1)C1=C(C=CC=C1)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-nitroaniline (0.41 g, 3.0 mmol) and methyl 4-chlorocarbonyl benzoate (0.65 g, 3.3 mmol) in THF (3.7 mL) and pyridine (0.8 mL) was stirred for 2 h at room temperature. The reaction was diluted with saturated sodium bicarbonate (10 mL) and EtOAc (15 mL), the phases separated and the aqueous phase extracte... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Primary amide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C([O-])(O)=O.[Na+].CCOC(=O)C.C1CCOC1 | null | null | COC(=O)c1ccc(C(=O)Cl)cc1.Nc1ccccc1[N+](=O)[O-]>C([O-])(O)=O.[Na+].CCOC(=O)C.C1CCOC1>COC(=O)c1ccc(C(N)=O)cc1-c1ccccc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d8a2c95828aa44b680e86701b63d239b | COC(=O)c1ccc(C(N)=O)cc1-c1ccccc1[N+](=O)[O-]>>COC(=O)c1ccc(-c2nc3ccccc3[nH]2)cc1 | COC(C1=C(C=C(C(=O)N)C=C1)C1=C(C=CC=C1)[N+](=O)[O-])=O.C(C)(=O)O>>N1=C(NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2 | O=[C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:19](-[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[N+:17](=O)[O-])[cH:18]1)[NH2:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[nH:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(C(N)=O)cc1-c1ccccc1[N+](=O)[O-] | COC(=O)c1ccc(-c2nc3ccccc3[nH]2)cc1 | null | [Fe] | null | Aromatic Heterocycle Formation | OtherReaction | 95a1b6a14ce4a9ec08dfb6887f0aff13fd3f99070de07be6c6a0bf0fb60dadc2 | 4dae36ec52719150ab4cf0197d9750f02baaebcb57163c373b47cefcd72f4cd8 | c1ccc(-c2nc3ccccc3[nH]2)cc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[c;H0;D3;+0:3]1:[c:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[N+;H0;D3:10](=O)-[O-]):[c:11]):[c:12](-[C:13](=[O;D1;H0:14])-[#8:15]-[C;D1;H3:16]):[c:17]:[c:18]:1>>[C;D1;H3:16]-[#8:15]-[C:13](=[O;D1;H0:14])-[c:12]1:[c:17]:[c:18]:[c;H0;D3;+0:3](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:2]:... | 86 | [{"value": 86.0, "product": "N1=C(NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (2-nitrophenyl)-terephthalamic acid methyl ester (0.23 g, 0.76 mmol) in glacial acetic acid (2.5 mL) was added iron powder (<5 μm mesh, 0.12 g, 2.1 mmol) and the mixture stirred at reflux for 1 h. The mixture was cooled, stirred at room temperature for 2 h and concentrated under reduced pressure. The r... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary amide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | [Fe] | null | null | COC(=O)c1ccc(C(N)=O)cc1-c1ccccc1[N+](=O)[O-]>[Fe]>COC(=O)c1ccc(-c2nc3ccccc3[nH]2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9063122c42f54bc49e4e673ee2153a6a | COC(=O)c1ccc(-c2nc3ccccc3[nH]2)cc1>>OCc1ccc(-c2nc3ccccc3[nH]2)cc1 | N1=C(NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2.CC(C)C[AlH]CC(C)C>>N1=C(NC2=C1C=CC=C2)C2=CC=C(CO)C=C2 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[nH:15]2)[cH:16][cH:17]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[nH:15]2)[cH:16][cH:17]1 | COC(=O)c1ccc(-c2nc3ccccc3[nH]2)cc1 | OCc1ccc(-c2nc3ccccc3[nH]2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2nc3ccccc3[nH]2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 87 | [{"value": 87.0, "product": "N1=C(NC2=C1C=CC=C2)C2=CC=C(CO)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "N1=C(NC2=C1C=CC=C2)C2=CC=C(CO)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of methyl 4-(benzimidazol-2-yl)-benzoate (0.23 g, 0.9 mmol) in THF (10 mL) at 0° C. was added a solution of DIBAL-H (5.0 mL, 1.0 M in THF, 5.0 mmol). The reaction was allowed to warm to room temperature, stirred for 1 h and quenched with a saturated potassium sodium tartrate solution (20 mL). The biphasic... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | C1CCOC1 | null | 1 | COC(=O)c1ccc(-c2nc3ccccc3[nH]2)cc1>C1CCOC1>OCc1ccc(-c2nc3ccccc3[nH]2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-952b8ed9281d4331b9d03bfc456f033a | OCc1ccc(-c2nc3ccccc3[nH]2)cc1>>O=Cc1ccc(-c2nc3ccccc3[nH]2)cc1 | N1=C(NC2=C1C=CC=C2)C2=CC=C(CO)C=C2>>N1=C(NC2=C1C=CC=C2)C2=CC=C(C=O)C=C2 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[nH:15]2)[cH:16][cH:17]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[nH:15]2)[cH:16][cH:17]1 | OCc1ccc(-c2nc3ccccc3[nH]2)cc1 | O=Cc1ccc(-c2nc3ccccc3[nH]2)cc1 | null | O=[Mn]=O | C1CCOC1.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-c2nc3ccccc3[nH]2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 42 | [{"value": 42.0, "product": "N1=C(NC2=C1C=CC=C2)C2=CC=C(C=O)C=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 4-(Benzimidazol-2-yl)-benzyl alcohol from above (0.175 g, 0.78 mmol) was dissolved in CH2Cl2 (5 mL) and THF (8 mL), treated with activated MnO2 (0.68 g, 7.8 mmol) and stirred at room temperature for 1.5 h. The mixture was filtered through celite, the cake washed with CH2Cl2 and the solvent from the eluent removed under... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | null | O=[Mn]=O.C1CCOC1.C(Cl)Cl | null | 1.5 | OCc1ccc(-c2nc3ccccc3[nH]2)cc1>O=[Mn]=O.C1CCOC1.C(Cl)Cl>O=Cc1ccc(-c2nc3ccccc3[nH]2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28f05a485ffe4b438d16539093f16f5b | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1ccc(-c2nc3ccccc3[nH]2)cc1>>CC(C)(C)OC(=O)n1c(CN(Cc2ccc(-c3nc4ccccc4[nH]3)cc2)C2CCCc3cccnc32)nc2ccccc21 | N1=C(NC2=C1C=CC=C2)C2=CC=C(C=O)C=C2.C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21.C(C)(=O)O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>N1C(=NC2=C1C=CC=C2)C2=CC=C(CN(C1CCCC=3C=CC=NC13)CC1=NC3=C(N1C(=O)OC(C)(C)C)C=CC=C3)C=C2 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[c:9]([CH2:10][NH:11][CH:28]2[CH2:29][CH2:30][CH2:31][c:32]3[cH:33][cH:34][cH:35][n:36][c:37]32)[n:38][c:39]2[cH:40][cH:41][cH:42][cH:43][c:44]12.O=[CH:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[nH:25]2)[cH:26][cH:27]1>>[... | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1ccc(-c2nc3ccccc3[nH]2)cc1 | CC(C)(C)OC(=O)n1c(CN(Cc2ccc(-c3nc4ccccc4[nH]3)cc2)C2CCCc3cccnc32)nc2ccccc21 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1cnc2c(c1)CCCC2N(Cc1ccc(-c2nc3ccccc3[nH]2)cc1)Cc1nc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[C:7](-[NH;D2;+0:8]-[C:9]-[c:10](:[#7;a:11]):[#7;a:12])-[C:13]>>[#7;a:5]:[c:6]-[C:7](-[N;H0;D3;+0:8](-[C:9]-[c:10](:[#7;a:11]):[#7;a:12])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:13] | 39 | [{"value": 39.0, "product": "N1C(=NC2=C1C=CC=C2)C2=CC=C(CN(C1CCCC=3C=CC=NC13)CC1=NC3=C(N1C(=O)OC(C)(C)C)C=CC=C3)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.1, "product": "N1C(=NC2=C1C=CC=C2)C2=CC=C(CN(C1CCCC=3C=CC=NC13)CC1=NC3=C(N1C(=O)OC(C)(C)C)C=CC=C3)C=C2", "details": "CALCULATEDPERCENTYIELD... | 60 | CELSIUS | 3 | HOUR | Using General Procedure B: To a solution 4-(benzimidazol-2-yl)-benzaldehyde (39 mg, 0.175 mmol) and (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (60 mg, 0.16 mmol) in THF (2 mL) was added acetic acid (90 μL) and sodium triacetoxyborohydride (68 mg, 0.32 mmol) and the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1cnc2c(c1)CCCC2.c1nc2ccccc2[nH]1 | Other | C1CCOC1 | 60 | 3 | CC(C)(C)OC(=O)n1c(CNC2CCCc3cccnc32)nc2ccccc21.O=Cc1ccc(-c2nc3ccccc3[nH]2)cc1>C1CCOC1>CC(C)(C)OC(=O)n1c(CN(Cc2ccc(-c3nc4ccccc4[nH]3)cc2)C2CCCc3cccnc32)nc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ed0169c98c6488d8dad8a0f33d78cb4 | COC(=O)c1ccc(Br)cc1.c1cocn1>>COC(=O)c1ccc(-c2ncco2)cc1 | O1C=NC=C1.C(CCC)[Li].COC(C1=CC=C(C=C1)Br)=O.C(CCC)[Li]>>COC(C1=CC=C(C=C1)C=1OC=CN1)=O | Br[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15][cH:14]1.[cH:9]1[n:10][cH:11][cH:12][o:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][cH:11][cH:12][o:13]2)[cH:14][cH:15]1 | COC(=O)c1ccc(Br)cc1.c1cocn1 | COC(=O)c1ccc(-c2ncco2)cc1 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cl-].[Zn+2].[Cl-] | C1CCOC1.C(C)(=O)OCC | C-C Coupling | OtherReaction | b8839202a1779fe713a2cb0d8e420a676e91f0069fad6c8a29a8e26eaadda799 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2ncco2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]1:[c:7]:[c:8]:[#8;a:9]:[cH;D2;+0:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]1:[#7;a:6]:[c:7]:[c:8]:[#8;a:9]:1):[c:4]:[c:5] | 42 | [{"value": 42.0, "product": "COC(C1=CC=C(C=C1)C=1OC=CN1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.8, "product": "COC(C1=CC=C(C=C1)C=1OC=CN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of oxazole (0.285 mL, 4 mmol) in THF (40 mL) at −78° C. was added n-butyllithium (1.83 mL of a 2.4M solution in hexanes, 4.4 mmol) and the reaction stirred for 30 min at −78° C. then zinc chloride (12 mL of 1M solution in THF, 12 mmol) was added. The mixture was then allowed to slowly warm to 0° C. and wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1cocn1 | c1ccccc1.c1cocn1 | c1ccccc1.c1cocn1 | HBr | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cl-].[Zn+2].[Cl-].C1CCOC1.C(C)(=O)OCC | -78 | 0.5 | COC(=O)c1ccc(Br)cc1.c1cocn1>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cl-].[Zn+2].[Cl-].C1CCOC1.C(C)(=O)OCC>COC(=O)c1ccc(-c2ncco2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85cb7c3d3f1440a8a446dd9990ca3e2b | COC(=O)c1ccc(-c2ncco2)cc1>>OCc1ccc(-c2ncco2)cc1 | COC(C1=CC=C(C=C1)C=1OC=CN1)=O.CC(C)C[AlH]CC(C)C>>O1C(=NC=C1)C1=CC=C(CO)C=C1 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][o:11]2)[cH:12][cH:13]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][o:11]2)[cH:12][cH:13]1 | COC(=O)c1ccc(-c2ncco2)cc1 | OCc1ccc(-c2ncco2)cc1 | null | null | ClCCl.C(Cl)Cl | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2ncco2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 89 | [{"value": 89.0, "product": "O1C(=NC=C1)C1=CC=C(CO)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "O1C(=NC=C1)C1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | To a solution of methyl-4-(oxazol-2-yl)-benzoate (0.203 g, 1 mmol) in CH2Cl2 (10 mL) 0° C. was added DIBAL-H (4 mL of a 1.0M solution in dichloromethane, 4 mmol) over 10 minutes. The resultant solution was stirred at 0° C. for 2 hours then quenched with an aqueous saturated solution of sodium potassium tartrate (20 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1cocn1 | Other | ClCCl.C(Cl)Cl | null | 1 | COC(=O)c1ccc(-c2ncco2)cc1>ClCCl.C(Cl)Cl>OCc1ccc(-c2ncco2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a2f34a04f1b42dcbdbae8ab9077148c | Brc1nccs1.O=Cc1ccc(B(O)O)cc1>>O=Cc1ccc(-c2nccs2)cc1 | BrC=1SC=CN1.C(=O)C1=CC=C(C=C1)B(O)O.C(=O)([O-])[O-].[K+].[K+]>>S1C(=NC=C1)C1=CC=C(C=O)C=C1 | Br[c:7]1[n:8][cH:9][cH:10][s:11]1.OB(O)[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:13][cH:12]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][s:11]2)[cH:12][cH:13]1 | Brc1nccs1.O=Cc1ccc(B(O)O)cc1 | O=Cc1ccc(-c2nccs2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C(C)(=O)OCC.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | f4565b4e9dabb73b09ab28617730b65da20c1e6e94d183a4606dbf1402c06c05 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nccs2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.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]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[c:9]:[c:10] | 15 | [{"value": 15.0, "product": "S1C(=NC=C1)C1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.9, "product": "S1C(=NC=C1)C1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-bromothiazole (0.26 g, 1.6 mmol) and 4-formylphenylboronic acid (0.48 g, 3.2 mmol) in toluene (16 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.09 g, 0.08 mmol) and K2CO3 (0.33 g, 2.4 mmol) and the solution stirred at reflux for 16 h. The reaction was cooled to room temperature, diluted w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cscn1.c1ccccc1 | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(C)(=O)OCC.C1(=CC=CC=C1)C | null | null | Brc1nccs1.O=Cc1ccc(B(O)O)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(C)(=O)OCC.C1(=CC=CC=C1)C>O=Cc1ccc(-c2nccs2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95e468a9fa17458cbc976ef761717842 | COC(=O)c1ccc(-c2nc3ccccc3s2)cc1>>OCc1ccc(-c2nc3ccccc3s2)cc1 | C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+].COC(C1=CC=C(C=C1)C=1SC2=C(N1)C=CC=C2)=O.CC(C)C[AlH]CC(C)C>>S1C(=NC2=C1C=CC=C2)C2=CC=C(CO)C=C2 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[s:15]2)[cH:16][cH:17]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[s:15]2)[cH:16][cH:17]1 | COC(=O)c1ccc(-c2nc3ccccc3s2)cc1 | OCc1ccc(-c2nc3ccccc3s2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2nc3ccccc3s2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 75 | [{"value": 75.0, "product": "S1C(=NC2=C1C=CC=C2)C2=CC=C(CO)C=C2", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a 0° C. solution of methyl-4-(benzothiazol-2-yl)-benzoate (prepared as described by A. Brembilla, D. Roizard and P. Lochon Synth. Commun. 1990, 20, 3379) (1.08 g, 4 mmol) in THF (20 mL) was added DIBAL-H (20 mL of a 1.0M solution in THF, 20 mmol) over 10 minutes. The resulting solution was stirred at 0° C. for 2 hou... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccc2scnc2c1 | Other | C1CCOC1 | 0 | 2 | COC(=O)c1ccc(-c2nc3ccccc3s2)cc1>C1CCOC1>OCc1ccc(-c2nc3ccccc3s2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8aadbbed1f9a4ba3955d9427ac7ecc89 | COC(=O)c1ccc(C(N)=O)cc1-c1ccccc1O>>COC(=O)c1ccc(-c2nc3ccccc3o2)cc1 | COC(C1=C(C=C(C(=O)N)C=C1)C1=C(C=CC=C1)O)=O.O.C(=O)([O-])[O-].[K+].[K+]>>O1C(=NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2 | O[c:16]1[c:11](-[c:19]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][c:8]([C:9]([NH2:10])=[O:17])[cH:18]2)[cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[o:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(C(N)=O)cc1-c1ccccc1O | COC(=O)c1ccc(-c2nc3ccccc3o2)cc1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | c652d532d45678c9eb1ee5d944d6e20c7429c9263fca6d58e700e5fe4da0ba62 | eeb5f637b347409f1b64d0e50278d8413c29899b416ed3c8145addccf705d03b | c1ccc(-c2nc3ccccc3o2)cc1 | O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:7]1:[c:8]:[c;H0;D3;+0:9](-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[O;H0;D1;+0:12]):[c:13]:[c:14]:[c:15]:1-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19]>>[C;D1;H3:19]-[#8:18]-[C:16](=[O;D1;H0:17])-[c:15]1:[c:14]:[c:13]:[c;H0;D3;+0:9](-[c;H0;D3;+0:10]2:[n;H0;D2... | 91.1 | [{"value": 45.0, "product": "O1C(=NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "O1C(=NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A solution of (2-hydroxyphenyl)-terephthalamic acid methyl ester (0.35 g, 1.3 mmol) in polyphosphoric acid (˜5 mL) was heated to reflux for 3 h. The solution was cooled to 0° C., water added (100 mL) and solid K2CO3 introduced until pH 7–9 was attained. The residue was diluted with ethyl acetate (2×100 mL) and the orga... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Aromatic alcohol | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccc2ocnc2c1 | c1ccccc1.c1ccc2ocnc2c1 | HO- | C(C)(=O)OCC | 0 | null | COC(=O)c1ccc(C(N)=O)cc1-c1ccccc1O>C(C)(=O)OCC>COC(=O)c1ccc(-c2nc3ccccc3o2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0439c2fefc7c49b5a81e78ca699c8b1a | COC(=O)c1ccc(-c2nc3ccccc3o2)cc1>>OCc1ccc(-c2nc3ccccc3o2)cc1 | O1C(=NC2=C1C=CC=C2)C2=CC=C(C(=O)OC)C=C2.CC(C)C[AlH]CC(C)C>>O1C(=NC2=C1C=CC=C2)C2=CC=C(CO)C=C2 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[o:15]2)[cH:16][cH:17]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[o:15]2)[cH:16][cH:17]1 | COC(=O)c1ccc(-c2nc3ccccc3o2)cc1 | OCc1ccc(-c2nc3ccccc3o2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2nc3ccccc3o2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 89 | [{"value": 89.0, "product": "O1C(=NC2=C1C=CC=C2)C2=CC=C(CO)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "O1C(=NC2=C1C=CC=C2)C2=CC=C(CO)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of methyl 4-(benzoxazol-2-yl)-benzoate (0.20 g, 0.8 mmol) in THF (8 mL) at −78° C. was added a solution of DIBAL-H (4.0 mL, 1.0 M in THF, 4.0 mmol). The reaction was allowed to warm to room temperature, stirred for 1 h and quenched with a saturated potassium sodium tartrate solution (15 mL). The biphasic ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccc2ocnc2c1 | Other | C1CCOC1 | null | 1 | COC(=O)c1ccc(-c2nc3ccccc3o2)cc1>C1CCOC1>OCc1ccc(-c2nc3ccccc3o2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6280e45839ed44b288894d446541a1ef | COc1ccccc1B(O)O.O=Cc1ccc(Br)cc1>>COc1ccccc1-c1ccc(C=O)cc1 | C(=O)([O-])[O-].[Na+].[Na+].BrC1=CC=C(C=O)C=C1.COC1=C(C=CC=C1)B(O)O>>COC1=C(C=CC=C1)C1=CC=C(C=C1)C=O | OB(O)[c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.Br[c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[cH:15][cH:16]1 | COc1ccccc1B(O)O.O=Cc1ccc(Br)cc1 | COc1ccccc1-c1ccc(C=O)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC.C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | 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](-[#8:10]):[c:11]>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 92 | [{"value": 92.0, "product": "COC1=C(C=CC=C1)C1=CC=C(C=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.8, "product": "COC1=C(C=CC=C1)C1=CC=C(C=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a stirred degassed solution of 4-bromobenzaldehyde (218 mg, 1.18 mmol) and 2-methoxybenzeneboronic acid (188 mg, 1.24 mmol) in DME/THF (5 mL, 4:1) were added a 2 M Na2CO3 solution (1.6 mL) and Pd(PPh3)4 (63 mg, 0.055 mmol). The reaction mixture was flushed with argon and maintained under argon while being heated at ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.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.COCCOC.C1CCOC1 | 85 | null | COc1ccccc1B(O)O.O=Cc1ccc(Br)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC.C1CCOC1>COc1ccccc1-c1ccc(C=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58d9d2451cc241dba47c7b8c690cd786 | OCc1ccc(-c2cnco2)cc1>>O=Cc1ccc(-c2cnco2)cc1 | O1C=NC=C1C1=CC=C(CO)C=C1>>O1C=NC=C1C1=CC=C(C=O)C=C1 | [OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][o:11]2)[cH:12][cH:13]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][o:11]2)[cH:12][cH:13]1 | OCc1ccc(-c2cnco2)cc1 | O=Cc1ccc(-c2cnco2)cc1 | null | O=[Mn]=O | C(Cl)Cl.C(Cl)Cl.CO | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-c2cnco2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | To a stirred solution of the 4-(oxazol-5-yl)benzyl alcohol (prepared as described by Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. J. Med. Chem. 1998, 41, 2390–2410) (0.23 g, 1.31 mmol) in CH2Cl2/MeOH (20:1, 10.5 mL) was added activated MnO2 (1.01 g, 11.6 mmol) and... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1cocn1 | null | O=[Mn]=O.C(Cl)Cl.C(Cl)Cl.CO | null | 8 | OCc1ccc(-c2cnco2)cc1>O=[Mn]=O.C(Cl)Cl.C(Cl)Cl.CO>O=Cc1ccc(-c2cnco2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-08b8e9673d45433fa9eb3ffb2e0655f3 | O=Cc1ccc(Br)cc1.OB(O)c1cccs1>>O=Cc1ccc(-c2cccs2)cc1 | C(=O)([O-])[O-].[Na+].[Na+].BrC1=CC=C(C=O)C=C1.S1C(=CC=C1)B(O)O>>S1C(=CC=C1)C1=CC=C(C=O)C=C1 | Br[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:13][cH:12]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][s:11]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][s:11]2)[cH:12][cH:13]1 | O=Cc1ccc(Br)cc1.OB(O)c1cccs1 | O=Cc1ccc(-c2cccs2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC.C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1):[c:4]:[c:5] | 78 | [{"value": 78.0, "product": "S1C(=CC=C1)C1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "S1C(=CC=C1)C1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a stirred degassed solution of 4-bromobenzaldehyde (371 mg, 2.00 mmol) and thiophene-2-boronic acid (287 mg, 2.24 mmol) in DME/THF (5 mL, 4:1) were added a 2 M Na2CO3 solution (3.0 mL) and Pd(PPh3)4 (110 mg, 0.095 mmol). The reaction mixture was flushed with argon and maintained under argon while being heated at 85°... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | 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.COCCOC.C1CCOC1 | 85 | null | O=Cc1ccc(Br)cc1.OB(O)c1cccs1>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.COCCOC.C1CCOC1>O=Cc1ccc(-c2cccs2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a13f63122e0f4a9ca6968c438395a964 | COC(=O)c1ccc(-c2ncc(-c3ccccc3)o2)cc1>>OCc1ccc(-c2ncc(-c3ccccc3)o2)cc1 | COC(C1=CC=C(C=C1)C=1OC(=CN1)C1=CC=CC=C1)=O.CC(C)C[AlH]CC(C)C.C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+]>>OCC1=CC=C(C=C1)C=1OC(=CN1)C1=CC=CC=C1 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[o:17]2)[cH:18][cH:19]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[o:17]2)[cH:18][cH:19]1 | COC(=O)c1ccc(-c2ncc(-c3ccccc3)o2)cc1 | OCc1ccc(-c2ncc(-c3ccccc3)o2)cc1 | null | null | C(Cl)Cl | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2cnc(-c3ccccc3)o2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | -78 | CELSIUS | 90 | MINUTE | To a solution of methyl-4-(5-phenyloxazol-2-yl)-benzoate (56 mg, 0.19 mmol) in CH2Cl2 (8 mL) at −78° C. was added DIBAL-H (1 mL of a 1.0 M solution in CH2Cl2, 1.0 mmol) and the solution stirred at −78° C. for 90 min. A saturated aqueous solution of sodium potassium tartrate (5 mL) was added to the reaction and the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1cocn1.c1ccccc1 | Other | C(Cl)Cl | -78 | 1.5 | COC(=O)c1ccc(-c2ncc(-c3ccccc3)o2)cc1>C(Cl)Cl>OCc1ccc(-c2ncc(-c3ccccc3)o2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8a93c2e2b784f2fbed88552562dcb80 | CC(=O)Cl.CNC.O=Cc1ccccc1>>C[N+](C)=Cc1ccccc1.[Cl-] | C(C)(=O)Cl.CNC.C(C1=CC=CC=C1)=O>>[Cl-].C(C1=CC=CC=C1)=[N+](C)C | CC(=O)[Cl:11].[CH3:1][NH:2][CH3:3].O=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[Cl-:11] | CC(=O)Cl.CNC.O=Cc1ccccc1 | C[N+](C)=Cc1ccccc1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | eff493add1f06df45aca8c74a1021d505d12a8600cde1bb3b6b0975b8d046526 | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | c1ccccc1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N+;H0;D3:7](-[C;D1;H3:8])=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[Cl-;H0;D0:1] | 70.7 | [{"value": 70.7, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 32.0 ml (0.213 mol) dimethylamine solution and 8.0 ml (0.079 mol) benzaldehyde in accordance with general synthesis instructions 1 and subsequent reaction with 4.7 ml (0.079 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 9.5 g (corresponding to 70.7% of the yield calculate... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)Cl.CNC.O=Cc1ccccc1>>C[N+](C)=Cc1ccccc1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72da6cfad289430d96716ceae4346d94 | CCOC(=O)c1cc2ccccc2[nH]1.C[N+](C)=Cc1ccccc1>>CCOC(=O)c1[nH]c2ccccc2c1C(c1ccccc1)N(C)C | C(C)OC(=O)C=1NC2=CC=CC=C2C1.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>C(C)OC(=O)C=1NC2=CC=CC=C2C1C(C1=CC=CC=C1)N(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1.[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)=[N+:22]([CH3:23])[CH3:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[N:2... | CCOC(=O)c1cc2ccccc2[nH]1.C[N+](C)=Cc1ccccc1 | CCOC(=O)c1[nH]c2ccccc2c1C(c1ccccc1)N(C)C | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[#7;a:13]:[c:14](:[c:15]):[c:16](:[c:17]):[cH;D2;+0:18]:1>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[#7;a:13]:[c:14](:[c:15]):[c:16](:[c:17]):[c;H0;D3;+0:18]:1-[CH;D3;+0:4](-[N;H0;D3;+0:2](-[C;D1;H3:1])-... | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1H-indole-2-carboxylic acid ethyl ester and benzylidene-dimethyl-ammonium chloride. For characterization, an ESI-MS was recorded:
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | null | null | null | CCOC(=O)c1cc2ccccc2[nH]1.C[N+](C)=Cc1ccccc1>>CCOC(=O)c1[nH]c2ccccc2c1C(c1ccccc1)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c19ce5b2ab74400bfa9da1319b50e23 | C[N+](C)=Cc1ccccc1.O=C(O)c1cc2ccccc2[nH]1>>CN(C)C(c1ccccc1)c1c(C(=O)O)[nH]c2ccccc12 | N1C(=CC2=CC=CC=C12)C(=O)O.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>CN(C)C(C1=C(NC2=CC=CC=C12)C(=O)O)C1=CC=CC=C1 | [CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[cH:11]1[c:12]([C:13](=[O:14])[OH:15])[nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[c:12]([C:13](=[O:14])[OH:15])[nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | C[N+](C)=Cc1ccccc1.O=C(O)c1cc2ccccc2[nH]1 | CN(C)C(c1ccccc1)c1c(C(=O)O)[nH]c2ccccc12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[O;D1;H0:8]=[C:9](-[O;D1;H1:10])-[c:11]1:[#7;a:12]:[c:13](:[c:14]):[c:15](:[c:16]):[cH;D2;+0:17]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:17]1:[c:11](-[C:9](=[O;D1;H0:8])-[O;D1;H1:10]):[#7;a:12]:[c:... | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1H-indole-2-carboxylic acid and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | C[N+](C)=Cc1ccccc1.O=C(O)c1cc2ccccc2[nH]1>>CN(C)C(c1ccccc1)c1c(C(=O)O)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1223901dad16410f8b88864e89634e05 | CCn1c(-c2ccccc2)cc2ccccc21.C[N+](C)=Cc1ccccc1>>CCn1c(-c2ccccc2)c(C(c2ccccc2)N(C)C)c2ccccc21 | C(C)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>C(C)N1C(=C(C2=CC=CC=C12)C(C1=CC=CC=C1)N(C)C)C1=CC=CC=C1 | [CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12.[CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[N+:19]([CH3:20])[CH3:21]>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]... | CCn1c(-c2ccccc2)cc2ccccc21.C[N+](C)=Cc1ccccc1 | CCn1c(-c2ccccc2)c(C(c2ccccc2)N(C)C)c2ccccc21 | null | null | null | C-C Coupling | OtherReaction | 69f18875ddec6b1e778b1d4e27c4b85fcc773368952787ad8942320571774e02 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:1-[c:16]>>[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[c;H0;D3;+0:14](-[CH;D3;+0:4](-[N;H0;D3;+0:2](-[C;D1;H3:1])-[C;D1;H3:3])-[c:5](:[c:6]):[c:7]):[c:15]:1-[c:16] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethyl-2-phenyl-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | null | null | null | null | CCn1c(-c2ccccc2)cc2ccccc21.C[N+](C)=Cc1ccccc1>>CCn1c(-c2ccccc2)c(C(c2ccccc2)N(C)C)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-534b098f3a2c49f69c538b07cabcb376 | COc1ccc2[nH]ccc2c1.C[N+](C)=Cc1ccccc1>>COc1ccc2[nH]cc(C(c3ccccc3)N(C)C)c2c1 | COC=1C=C2C=CNC2=CC1.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>COC=1C=C2C(=CNC2=CC1)C(C1=CC=CC=C1)N(C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:20]2[cH:21]1.[CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[N+:17]([CH3:18])[CH3:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([CH:10]([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[N:17]([CH3:18])[CH3:19])[c:20]2[cH:21]1 | COc1ccc2[nH]ccc2c1.C[N+](C)=Cc1ccccc1 | COc1ccc2[nH]cc(C(c3ccccc3)N(C)C)c2c1 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11]:[#7;a:12]:[c:13]:1:[c:14]>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:9]:1:[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-methoxy-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | null | null | null | COc1ccc2[nH]ccc2c1.C[N+](C)=Cc1ccccc1>>COc1ccc2[nH]cc(C(c3ccccc3)N(C)C)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e35ed87604f84e598d86fcf78697f08e | C[N+](C)=Cc1ccccc1.O=C(O)c1cc2cc(O)ccc2[nH]1>>CN(C)C(c1ccccc1)c1c(C(=O)O)[nH]c2ccc(O)cc12 | OC=1C=C2C=C(NC2=CC1)C(=O)O.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>CN(C)C(C1=C(NC2=CC=C(C=C12)O)C(=O)O)C1=CC=CC=C1 | [CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[cH:11]1[c:12]([C:13](=[O:14])[OH:15])[nH:16][c:17]2[cH:18][cH:19][c:20]([OH:21])[cH:22][c:23]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[c:12]([C:13](=[O:14])[OH:15])[nH:16][c:17]2[cH:18][cH:19][c:20]([OH:21])[cH:22]... | C[N+](C)=Cc1ccccc1.O=C(O)c1cc2cc(O)ccc2[nH]1 | CN(C)C(c1ccccc1)c1c(C(=O)O)[nH]c2ccc(O)cc12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[O;D1;H0:8]=[C:9](-[O;D1;H1:10])-[c:11]1:[#7;a:12]:[c:13](:[c:14]):[c:15](:[c:16]):[cH;D2;+0:17]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:17]1:[c:11](-[C:9](=[O;D1;H0:8])-[O;D1;H1:10]):[#7;a:12]:[c:... | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-hydroxy-1H-indole-2-carboxylic acid and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | C[N+](C)=Cc1ccccc1.O=C(O)c1cc2cc(O)ccc2[nH]1>>CN(C)C(c1ccccc1)c1c(C(=O)O)[nH]c2ccc(O)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e385ae51537746cd8962eb40b5c4ef0d | C[N+](C)=Cc1ccccc1.Cc1cc2ccccc2[nH]1>>Cc1[nH]c2ccccc2c1C(c1ccccc1)N(C)C | CC=1NC2=CC=CC=C2C1.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>CN(C(C1=CC=CC=C1)C1=C(NC2=CC=CC=C12)C)C | [CH:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[N+:18]([CH3:19])[CH3:20].[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[cH:10]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]1[CH:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[N:18]([CH3:19])[CH3:20] | C[N+](C)=Cc1ccccc1.Cc1cc2ccccc2[nH]1 | Cc1[nH]c2ccccc2c1C(c1ccccc1)N(C)C | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:15]1:[c:9](-[C;D1;H3:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | null | null | null | C[N+](C)=Cc1ccccc1.Cc1cc2ccccc2[nH]1>>Cc1[nH]c2ccccc2c1C(c1ccccc1)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0be84a70ba3545d5b8875c78bac9b1ac | C[N+](C)=Cc1ccccc1.Oc1cccc2[nH]ccc12>>CN(C)C(c1ccccc1)c1c[nH]c2cccc(O)c12 | OC1=C2C=CNC2=CC=C1.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>CN(C)C(C1=CNC=2C=CC=C(C12)O)C1=CC=CC=C1 | [CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[cH:11]1[cH:12][nH:13][c:14]2[cH:15][cH:16][cH:17][c:18]([OH:19])[c:20]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][nH:13][c:14]2[cH:15][cH:16][cH:17][c:18]([OH:19])[c:20]12 | C[N+](C)=Cc1ccccc1.Oc1cccc2[nH]ccc12 | CN(C)C(c1ccccc1)c1c[nH]c2cccc(O)c12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-hydroxy-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | C[N+](C)=Cc1ccccc1.Oc1cccc2[nH]ccc12>>CN(C)C(c1ccccc1)c1c[nH]c2cccc(O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-15cb9b2285214b0198c4d91d20a3fcb1 | C[N+](C)=Cc1ccccc1.Clc1ccc2[nH]ccc2c1>>CN(C)C(c1ccccc1)c1c[nH]c2ccc(Cl)cc12 | ClC=1C=C2C=CNC2=CC1.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>ClC=1C=C2C(=CNC2=CC1)C(C1=CC=CC=C1)N(C)C | [CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[cH:11]1[cH:12][nH:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][nH:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]12 | C[N+](C)=Cc1ccccc1.Clc1ccc2[nH]ccc2c1 | CN(C)C(c1ccccc1)c1c[nH]c2ccc(Cl)cc12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-chloro-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | C[N+](C)=Cc1ccccc1.Clc1ccc2[nH]ccc2c1>>CN(C)C(c1ccccc1)c1c[nH]c2ccc(Cl)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-84e9a07ef0414834be82c2870362ad02 | CC(=O)Oc1cccc2[nH]ccc12.C[N+](C)=Cc1ccccc1>>CC(=O)Oc1cccc2[nH]cc(C(c3ccccc3)N(C)C)c12 | N1C=CC2=C(C=CC=C12)OC(C)=O.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>CN(C)C(C1=CNC2=CC=CC(=C12)OC(C)=O)C1=CC=CC=C1 | [CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][cH:11][cH:12][c:23]12.[CH:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)=[N+:20]([CH3:21])[CH3:22]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][cH:11][c:12]([CH:13]([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[N:20]([CH3:21])[CH3:22])[c... | CC(=O)Oc1cccc2[nH]ccc12.C[N+](C)=Cc1ccccc1 | CC(=O)Oc1cccc2[nH]cc(C(c3ccccc3)N(C)C)c12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11]:[#7;a:12]:[c:13]:1:[c:14]>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:9]:1:[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from acetic acid 1H-indol-4-yl ester and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with exampl... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | null | null | null | CC(=O)Oc1cccc2[nH]ccc12.C[N+](C)=Cc1ccccc1>>CC(=O)Oc1cccc2[nH]cc(C(c3ccccc3)N(C)C)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3e9f91744aff4bafad71878515c662bd | C[N+](C)=Cc1ccccc1.Clc1ccc(-c2cc3ccccc3[nH]2)cc1>>CN(C)C(c1ccccc1)c1c(-c2ccc(Cl)cc2)[nH]c2ccccc12 | ClC1=CC=C(C=C1)C=1NC2=CC=CC=C2C1.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>ClC1=CC=C(C=C1)C=1NC2=CC=CC=C2C1C(C1=CC=CC=C1)N(C)C | [CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[cH:11]1[c:12](-[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[nH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[c:12](-[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]... | C[N+](C)=Cc1ccccc1.Clc1ccc(-c2cc3ccccc3[nH]2)cc1 | CN(C)C(c1ccccc1)c1c(-c2ccc(Cl)cc2)[nH]c2ccccc12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:15]1:[c:9](-[c:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-(4-chlorophenyl)-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | C[N+](C)=Cc1ccccc1.Clc1ccc(-c2cc3ccccc3[nH]2)cc1>>CN(C)C(c1ccccc1)c1c(-c2ccc(Cl)cc2)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a26ba1aa91024edd8cc9a52003c2eac1 | C[N+](C)=Cc1ccccc1.O=C(O)c1cc2cc(OCc3ccccc3)ccc2[nH]1>>CN(C)C(c1ccccc1)c1c(C(=O)O)[nH]c2ccc(OCc3ccccc3)cc12 | C(C1=CC=CC=C1)OC=1C=C2C=C(NC2=CC1)C(=O)O.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>C(C1=CC=CC=C1)OC=1C=C2C(=C(NC2=CC1)C(=O)O)C(C1=CC=CC=C1)N(C)C | [CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[cH:11]1[c:12]([C:13](=[O:14])[OH:15])[nH:16][c:17]2[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][c:30]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[c:12]([C:13](=[O:14])[OH:15])... | C[N+](C)=Cc1ccccc1.O=C(O)c1cc2cc(OCc3ccccc3)ccc2[nH]1 | CN(C)C(c1ccccc1)c1c(C(=O)O)[nH]c2ccc(OCc3ccccc3)cc12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(COc2ccc3[nH]cc(Cc4ccccc4)c3c2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[O;D1;H0:8]=[C:9](-[O;D1;H1:10])-[c:11]1:[#7;a:12]:[c:13](:[c:14]):[c:15](:[c:16]):[cH;D2;+0:17]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:17]1:[c:11](-[C:9](=[O;D1;H0:8])-[O;D1;H1:10]):[#7;a:12]:[c:... | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-benzyloxy-1H-indole-2-carboxylic acid and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance wit... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | null | null | null | null | C[N+](C)=Cc1ccccc1.O=C(O)c1cc2cc(OCc3ccccc3)ccc2[nH]1>>CN(C)C(c1ccccc1)c1c(C(=O)O)[nH]c2ccc(OCc3ccccc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ee61190596024eeb8d48adec2e37d056 | C[N+](C)=Cc1ccccc1.Cc1cc2cc([N+](=O)[O-])ccc2[nH]1>>Cc1[nH]c2ccc([N+](=O)[O-])cc2c1C(c1ccccc1)N(C)C | CC=1NC2=CC=C(C=C2C1)[N+](=O)[O-].[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>CN(C(C1=CC=CC=C1)C1=C(NC2=CC=C(C=C12)[N+](=O)[O-])C)C | [CH:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[N+:21]([CH3:22])[CH3:23].[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]2[cH:13]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]2[c:13]1[CH:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[N:21]([CH3:22... | C[N+](C)=Cc1ccccc1.Cc1cc2cc([N+](=O)[O-])ccc2[nH]1 | Cc1[nH]c2ccc([N+](=O)[O-])cc2c1C(c1ccccc1)N(C)C | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[CH;D3;+0:4](-[N;H0;D3;+0:2](-[C;D1;H3:1])-[C;D1;H3:3])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-5-nitro-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | null | null | null | C[N+](C)=Cc1ccccc1.Cc1cc2cc([N+](=O)[O-])ccc2[nH]1>>Cc1[nH]c2ccc([N+](=O)[O-])cc2c1C(c1ccccc1)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a14dcd750a5843378b734cc81f27f6c0 | C[N+](C)=Cc1ccccc1.Fc1ccc(-c2cc3ccccc3[nH]2)cc1Cl>>CN(C)C(c1ccccc1)c1c(-c2ccc(F)c(Cl)c2)[nH]c2ccccc12 | ClC=1C=C(C=CC1F)C=1NC2=CC=CC=C2C1.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>ClC=1C=C(C=CC1F)C=1NC2=CC=CC=C2C1C(C1=CC=CC=C1)N(C)C | [CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[cH:11]1[c:12](-[c:13]2[cH:14][cH:15][c:16]([F:17])[c:18]([Cl:19])[cH:20]2)[nH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[c:12](-[c:13]2[cH:14][cH:15][c:16]([F:17])[c:18]([... | C[N+](C)=Cc1ccccc1.Fc1ccc(-c2cc3ccccc3[nH]2)cc1Cl | CN(C)C(c1ccccc1)c1c(-c2ccc(F)c(Cl)c2)[nH]c2ccccc12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:15]1:[c:9](-[c:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-(3-chloro-4-fluorophenyl)-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | C[N+](C)=Cc1ccccc1.Fc1ccc(-c2cc3ccccc3[nH]2)cc1Cl>>CN(C)C(c1ccccc1)c1c(-c2ccc(F)c(Cl)c2)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-591a0661861d4211a8b3ee535d48f8a7 | CCc1cccc2cc[nH]c12.C[N+](C)=Cc1ccccc1>>CCc1cccc2c(C(c3ccccc3)N(C)C)c[nH]c12 | C(C)C=1C=CC=C2C=CNC12.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>C(C)C=1C=CC=C2C(=CNC12)C(C1=CC=CC=C1)N(C)C | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:19][nH:20][c:21]12.[CH:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[N+:16]([CH3:17])[CH3:18]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[N:16]([CH3:17])[CH3:18])[cH:19][nH:20][c:21]12 | CCc1cccc2cc[nH]c12.C[N+](C)=Cc1ccccc1 | CCc1cccc2c(C(c3ccccc3)N(C)C)c[nH]c12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 7-ethyl-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | CCc1cccc2cc[nH]c12.C[N+](C)=Cc1ccccc1>>CCc1cccc2c(C(c3ccccc3)N(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7201ea0d60174d3f87bb02bbc4e730d0 | C[N+](C)=Cc1ccccc1.O=C(O)c1ccc2cc[nH]c2c1>>CN(C)C(c1ccccc1)c1c[nH]c2cc(C(=O)O)ccc12 | N1C=CC2=CC=C(C=C12)C(=O)O.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>CN(C)C(C1=CNC2=CC(=CC=C12)C(=O)O)C1=CC=CC=C1 | [CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[cH:11]1[cH:12][nH:13][c:14]2[cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21][c:22]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][nH:13][c:14]2[cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21][c:22]12 | C[N+](C)=Cc1ccccc1.O=C(O)c1ccc2cc[nH]c2c1 | CN(C)C(c1ccccc1)c1c[nH]c2cc(C(=O)O)ccc12 | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1H-indole-6-carboxylic acid and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | C[N+](C)=Cc1ccccc1.O=C(O)c1ccc2cc[nH]c2c1>>CN(C)C(c1ccccc1)c1c[nH]c2cc(C(=O)O)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2c82f1e0a8e471f948109909b31a5ff | C[N+](C)=Cc1ccccc1.Cn1ccc2ccccc21>>CN(C)C(c1ccccc1)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].C(C1=CC=CC=C1)=[N+](C)C>>CN(C(C1=CC=CC=C1)C1=CN(C2=CC=CC=C12)C)C | [CH3:1][N+:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[cH:11]1[cH:12][n:13]([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][n:13]([CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12 | C[N+](C)=Cc1ccccc1.Cn1ccc2ccccc21 | CN(C)C(c1ccccc1)c1cn(C)c2ccccc12 | null | null | null | C-C Coupling | OtherReaction | 3ed07d2d6275586c1c2f5d2532fbab498e9d3e4f5deb2be25e45b589d2655d73 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C;D1;H3:9]-[N+;H0;D3:10](-[C;D1;H3:11])=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[c;H0;D3;+0:4](-[CH;D3;+0:12](-[N;H0;D3;+0:10](-[C;D1;H3:9])-[C;D1;H3:11])-[c:13](:[c:14]):[c:15]):[c:5](:[c:6]):[c:7]:1:[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methyl-1H-indole and benzylidene-dimethyl-ammonium chloride, which had been prepared in accordance with example 1.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 1 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | null | null | null | null | C[N+](C)=Cc1ccccc1.Cn1ccc2ccccc21>>CN(C)C(c1ccccc1)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-57d27ffc4b5149fd91ae99d5b4e5daf3 | C1COCCN1.CC(=O)Cl.O=Cc1ccccc1>>C(c1ccccc1)=[N+]1CCOCC1.[Cl-] | C(C)(=O)Cl.N1CCOCC1.C(C1=CC=CC=C1)=O>>[Cl-].C(C1=CC=CC=C1)=[N+]1CCOCC1 | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.CC(=O)[Cl:14].O=[CH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1>>[CH:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)=[N+:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.[Cl-:14] | C1COCCN1.CC(=O)Cl.O=Cc1ccccc1 | C(c1ccccc1)=[N+]1CCOCC1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 31879dca4a54a4198f28c09fb4ae420146eea69dd90827d43c74275f7a7a1a1d | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | C(c1ccccc1)=[N+]1CCOCC1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[Cl-;H0;D0:1].[c:4]:[c:3](-[CH;D2;+0:2]=[N+;H0;D3:9]1-[C:10]-[C:11]-[#8:6]-[C:7]-[C:8]-1):[c:5] | 48 | [{"value": 48.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 17.9 ml (0.200 mol) morpholine and 10.1 ml (0.100 mol) benzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 6.0 ml (0.100 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 10.1 g (corresponding to 48% of the yield calculated by theory)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | C1COCCN1 | C1COCC[NH+]1 | c1ccccc1.C1COCC[NH+]1 | HO- | null | null | null | C1COCCN1.CC(=O)Cl.O=Cc1ccccc1>>C(c1ccccc1)=[N+]1CCOCC1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-507d36ce993f4e09aa998eb3345b6674 | C(c1ccccc1)=[N+]1CCOCC1.Cn1ccc2ccccc21>>Cn1cc(C(c2ccccc2)N2CCOCC2)c2ccccc21 | CN1C=CC2=CC=CC=C12.[Cl-].C(C1=CC=CC=C1)=[N+]1CCOCC1>>CN1C=C(C2=CC=CC=C12)C(C1=CC=CC=C1)N1CCOCC1 | [CH:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)=[N+:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1.[CH3:1][n:2]1[cH:3][cH:4][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][n:2]1[cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22]... | C(c1ccccc1)=[N+]1CCOCC1.Cn1ccc2ccccc21 | Cn1cc(C(c2ccccc2)N2CCOCC2)c2ccccc21 | null | null | null | C-C Coupling | OtherReaction | 173b618d3281a9741e04b9a97313945326dc1997ca80037fb55f8e60c371ffba | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(C(c2c[nH]c3ccccc23)N2CCOCC2)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[c:9]:[c:10](-[CH;D2;+0:11]=[N+;H0;D3:12]1-[C:13]-[C:14]-[#8:15]-[C:16]-[C:17]-1):[c:18]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[c;H0;D3;+0:4](-[CH;D3;+0:11](-[N;H0;D3;+0:12]2-[C:13]-[C:14]-[#8:15]-[C:16]-[C:17]-2)-[c:10](:[c:9]):[c:18]):[c:5](:[c:6]):[c:7]:1:[... | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methyl-1H-indole and 4-benzylidene-morpholin-4-ium chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1COCC[NH+]1.c1ccc2[nH]ccc2c1 | C1COCC[NH]1.c1c[nH]c2ccccc12 | c1ccccc1.C1COCC[NH]1.c1c[nH]c2ccccc12 | null | null | null | null | C(c1ccccc1)=[N+]1CCOCC1.Cn1ccc2ccccc21>>Cn1cc(C(c2ccccc2)N2CCOCC2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c64f81c0b04347839e9f8f49788d19e9 | C1CCNC1.CC(=O)Cl.COc1ccccc1C=O>>COc1ccccc1C=[N+]1CCCC1.[Cl-] | C(C)(=O)Cl.N1CCCC1.COC1=C(C=O)C=CC=C1>>[Cl-].COC1=C(C=[N+]2CCCC2)C=CC=C1 | [NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1.CC(=O)[Cl:15].O=[CH:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1.[Cl-:15] | C1CCNC1.CC(=O)Cl.COc1ccccc1C=O | COc1ccccc1C=[N+]1CCCC1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3185d10eb773ba97ec1fc383b83b48bc84c0512494aaf7a724a2330b6e71ba2b | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | C(c1ccccc1)=[N+]1CCCC1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[Cl-;H0;D0:1].[c:4]:[c:3](-[CH;D2;+0:2]=[N+;H0;D3:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1):[c:5] | 78 | [{"value": 78.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 6.9 ml (0.084 mol) pyrrolidine and 4.8 g (0.035 mol) 2-methoxybenzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 2.1 ml (0.035 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 6.2 g (corresponding to 78% of the yield calculated by t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | C1CCNC1 | C1CC[NH+]C1 | c1ccccc1.C1CC[NH+]C1 | HO- | null | null | null | C1CCNC1.CC(=O)Cl.COc1ccccc1C=O>>COc1ccccc1C=[N+]1CCCC1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-211178e8e66b40dc95d56af13d564324 | COc1ccccc1C=[N+]1CCCC1.Cn1ccc2ccccc21>>COc1ccccc1C(c1cn(C)c2ccccc12)N1CCCC1 | CN1C=CC2=CC=CC=C12.[Cl-].COC1=C(C=[N+]2CCCC2)C=CC=C1>>COC1=C(C=CC=C1)C(C1=CN(C2=CC=CC=C12)C)N1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1.[cH:10]1[cH:11][n:12]([CH3:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([c:10]1[cH:11][n:12]([CH3:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12)[N:20]1[CH2:21][CH... | COc1ccccc1C=[N+]1CCCC1.Cn1ccc2ccccc21 | COc1ccccc1C(c1cn(C)c2ccccc12)N1CCCC1 | null | null | null | C-C Coupling | OtherReaction | 84c54d442d75f222c0e77a7abf5e6087a4c3e8e257e7a07ce913ea8c4dc96781 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(C(c2c[nH]c3ccccc23)N2CCCC2)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[c:9]:[c:10](-[CH;D2;+0:11]=[N+;H0;D3:12]1-[C:13]-[C:14]-[C:15]-[C:16]-1):[c:17]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[c;H0;D3;+0:4](-[CH;D3;+0:11](-[N;H0;D3;+0:12]2-[C:13]-[C:14]-[C:15]-[C:16]-2)-[c:10](:[c:9]):[c:17]):[c:5](:[c:6]):[c:7]:1:[c:8] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methyl-1H-indole and 1-(2-methoxy-benzylidene)-pyrrolidinium chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]C1.c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12.C1CC[NH]C1 | c1ccccc1.c1c[nH]c2ccccc12.C1CC[NH]C1 | null | null | null | null | COc1ccccc1C=[N+]1CCCC1.Cn1ccc2ccccc21>>COc1ccccc1C(c1cn(C)c2ccccc12)N1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d745609141254580931317ff1b8db479 | C1CCNC1.CC(=O)Cl.Cc1ccccc1C=O>>Cc1ccccc1C=[N+]1CCCC1.[Cl-] | C(C)(=O)Cl.N1CCCC1.CC1=C(C=O)C=CC=C1>>[Cl-].CC1=C(C=[N+]2CCCC2)C=CC=C1 | [NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1.CC(=O)[Cl:14].O=[CH:8][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1.[Cl-:14] | C1CCNC1.CC(=O)Cl.Cc1ccccc1C=O | Cc1ccccc1C=[N+]1CCCC1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3185d10eb773ba97ec1fc383b83b48bc84c0512494aaf7a724a2330b6e71ba2b | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | C(c1ccccc1)=[N+]1CCCC1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[Cl-;H0;D0:1].[c:4]:[c:3](-[CH;D2;+0:2]=[N+;H0;D3:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1):[c:5] | 63 | [{"value": 63.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 8.2 ml (0.100 mol) pyrrolidine and 7.0 g (0.050 mol) 2-methylbenzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 3.9 g (0.050 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 6.6 g (corresponding to 63% of the yield calculated by the... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | C1CCNC1 | C1CC[NH+]C1 | c1ccccc1.C1CC[NH+]C1 | HO- | null | null | null | C1CCNC1.CC(=O)Cl.Cc1ccccc1C=O>>Cc1ccccc1C=[N+]1CCCC1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51710e2fadba4c6ebef8fb7d62ebc731 | CCn1c(-c2ccccc2)cc2ccccc21.Cc1ccccc1C=[N+]1CCCC1>>CCn1c(-c2ccccc2)c(C(c2ccccc2C)N2CCCC2)c2ccccc21 | C(C)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1.[Cl-].CC1=C(C=[N+]2CCCC2)C=CC=C1>>C(C)N1C(=C(C2=CC=CC=C12)C(C1=C(C=CC=C1)C)N1CCCC1)C1=CC=CC=C1 | [CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]12.[CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[CH3:19])=[N+:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH:12]([c:13]2[cH:14][cH:1... | CCn1c(-c2ccccc2)cc2ccccc21.Cc1ccccc1C=[N+]1CCCC1 | CCn1c(-c2ccccc2)c(C(c2ccccc2C)N2CCCC2)c2ccccc21 | null | null | null | C-C Coupling | OtherReaction | d9d0c5bf4fd4ce1384bf9b4ff949b67b0d13d4469f030dfb035f0b60a70cd412 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-c2[nH]c3ccccc3c2C(c2ccccc2)N2CCCC2)cc1 | [C:1]-[#7;a:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:1-[c:9].[c:10]:[c:11](-[CH;D2;+0:12]=[N+;H0;D3:13]1-[C:14]-[C:15]-[C:16]-[C:17]-1):[c:18]>>[C:1]-[#7;a:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](-[CH;D3;+0:12](-[N;H0;D3;+0:13]2-[C:14]-[C:15]-[C:16]-[C:17]-2)-[c:11](:[c:10]):[c:18]):[c:8]:1-[c:9] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethyl-2-phenyl-1H-indole and 1-(2-methyl-benzylidene)-pyrrolidinium chloride
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2ccccc2[nH]1.C1CC[NH+]C1 | C1CC[NH]C1.c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1cc2ccccc2[nH]1 | null | null | null | null | CCn1c(-c2ccccc2)cc2ccccc21.Cc1ccccc1C=[N+]1CCCC1>>CCn1c(-c2ccccc2)c(C(c2ccccc2C)N2CCCC2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b6f01e61c48544b0ba58cf7e12990b46 | C1CCNCC1.CC(=O)Cl.O=Cc1ccccc1Cl>>Clc1ccccc1C=[N+]1CCCCC1.[Cl-] | C(C)(=O)Cl.N1CCCCC1.ClC1=C(C=O)C=CC=C1>>[Cl-].ClC1=C(C=[N+]2CCCCC2)C=CC=C1 | [NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1.CC(=O)[Cl:15].O=[CH:8][c:7]1[c:2]([Cl:1])[cH:3][cH:4][cH:5][cH:6]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1.[Cl-:15] | C1CCNCC1.CC(=O)Cl.O=Cc1ccccc1Cl | Clc1ccccc1C=[N+]1CCCCC1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | faf4b88da581351d4769fed76c5dc27494cac21b814d3867cba4e9d5df33e907 | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | C(c1ccccc1)=[N+]1CCCCC1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N+;H0;D3:8](=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5])-[C:9]-[C:10].[Cl-;H0;D0:1] | 58 | [{"value": 58.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 8.5 g (0.100 mol) piperidine and 7.0 g (0.050 mol) 2-chlorobenzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 3.9 g (0.050 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 7.1 g (corresponding to 58% of the yield calculated by theor... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | C1CCNCC1 | C1CC[NH+]CC1 | c1ccccc1.C1CC[NH+]CC1 | HO- | null | null | null | C1CCNCC1.CC(=O)Cl.O=Cc1ccccc1Cl>>Clc1ccccc1C=[N+]1CCCCC1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff9a8d4fad55412297bdb1e95d7c1e2d | CCn1c(-c2ccccc2)cc2ccccc21.Clc1ccccc1C=[N+]1CCCCC1>>CCn1c(-c2ccccc2)c(C(c2ccccc2Cl)N2CCCCC2)c2ccccc21 | C(C)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1.[Cl-].ClC1=C(C=[N+]2CCCCC2)C=CC=C1>>ClC1=C(C=CC=C1)C(C1=C(N(C2=CC=CC=C12)CC)C1=CC=CC=C1)N1CCCCC1 | [CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]12.[CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19])=[N+:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH:12]([c:13]2[cH:1... | CCn1c(-c2ccccc2)cc2ccccc21.Clc1ccccc1C=[N+]1CCCCC1 | CCn1c(-c2ccccc2)c(C(c2ccccc2Cl)N2CCCCC2)c2ccccc21 | null | null | null | C-C Coupling | OtherReaction | a6029a55f410aa4d99e8b11dc21cabdcdfffe21c2843f92c3f758c63bfa4bc6c | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-c2[nH]c3ccccc3c2C(c2ccccc2)N2CCCCC2)cc1 | [C:1]-[#7;a:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:1-[c:9].[C:10]-[C:11]-[N+;H0;D3:12](=[CH;D2;+0:13]-[c:14](:[c:15]):[c:16])-[C:17]-[C:18]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[CH;D3;+0:13](-[c:14](:[c:15]):[c:16])-[c;H0;D3;+0:7]1:[c:5](:[c:6]):[c:3](:[c:4]):[#7;a:2](-[C:1]):[c:8]:1-[c:9])-[C:17]-[C:18] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethyl-2-phenyl-1H-indole and 1-(2-chloro-benzylidene)-piperidinium chloride
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2ccccc2[nH]1.C1CC[NH+]CC1 | C1CC[NH]CC1.c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1cc2ccccc2[nH]1 | null | null | null | null | CCn1c(-c2ccccc2)cc2ccccc21.Clc1ccccc1C=[N+]1CCCCC1>>CCn1c(-c2ccccc2)c(C(c2ccccc2Cl)N2CCCCC2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55eedef74ef9485e918bed4ebdb783d6 | C1CCNC1.CC(=O)Cl.O=Cc1ccccc1>>C(c1ccccc1)=[N+]1CCCC1.[Cl-] | C(C)(=O)Cl.N1CCCC1.C(C1=CC=CC=C1)=O>>[Cl-].C(C1=CC=CC=C1)=[N+]1CCCC1 | [NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1.CC(=O)[Cl:13].O=[CH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1>>[CH:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)=[N+:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1.[Cl-:13] | C1CCNC1.CC(=O)Cl.O=Cc1ccccc1 | C(c1ccccc1)=[N+]1CCCC1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3185d10eb773ba97ec1fc383b83b48bc84c0512494aaf7a724a2330b6e71ba2b | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | C(c1ccccc1)=[N+]1CCCC1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-1>>[Cl-;H0;D0:1].[c:4]:[c:3](-[CH;D2;+0:2]=[N+;H0;D3:9]1-[C:8]-[C:7]-[C:6]-[C:10]-1):[c:5] | 72 | [{"value": 72.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 16.4 ml (0.200 mol) pyrrolidine and 10.1 ml (0.100 mol) benzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 6.0 ml (0.100 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 14.1 g (corresponding to 72% of the yield calculated by theory... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | C1CCNC1 | C1CC[NH+]C1 | c1ccccc1.C1CC[NH+]C1 | HO- | null | null | null | C1CCNC1.CC(=O)Cl.O=Cc1ccccc1>>C(c1ccccc1)=[N+]1CCCC1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26a143923e5c487886f1cf561a959abe | C(c1ccccc1)=[N+]1CCCC1.CCn1c(-c2ccccc2)cc2ccccc21>>CCn1c(-c2ccccc2)c(C(c2ccccc2)N2CCCC2)c2ccccc21 | C(C)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1.[Cl-].C(C1=CC=CC=C1)=[N+]1CCCC1>>C(C)N1C(=C(C2=CC=CC=C12)C(N1CCCC1)C1=CC=CC=C1)C1=CC=CC=C1 | [CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[N+:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1.[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]12>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH:12]([c:13]2[cH:14][cH:15][cH:1... | C(c1ccccc1)=[N+]1CCCC1.CCn1c(-c2ccccc2)cc2ccccc21 | CCn1c(-c2ccccc2)c(C(c2ccccc2)N2CCCC2)c2ccccc21 | null | null | null | C-C Coupling | OtherReaction | d9d0c5bf4fd4ce1384bf9b4ff949b67b0d13d4469f030dfb035f0b60a70cd412 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-c2[nH]c3ccccc3c2C(c2ccccc2)N2CCCC2)cc1 | [C:1]-[#7;a:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:1-[c:9].[c:10]:[c:11](-[CH;D2;+0:12]=[N+;H0;D3:13]1-[C:14]-[C:15]-[C:16]-[C:17]-1):[c:18]>>[C:1]-[#7;a:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](-[CH;D3;+0:12](-[N;H0;D3;+0:13]2-[C:14]-[C:15]-[C:16]-[C:17]-2)-[c:11](:[c:10]):[c:18]):[c:8]:1-[c:9] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethyl-2-phenyl-1H-indole and 1-benzylidene-pyrrolidinium chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]C1.c1cc2ccccc2[nH]1 | C1CC[NH]C1.c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1cc2ccccc2[nH]1 | null | null | null | null | C(c1ccccc1)=[N+]1CCCC1.CCn1c(-c2ccccc2)cc2ccccc21>>CCn1c(-c2ccccc2)c(C(c2ccccc2)N2CCCC2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-906dadc4729b47dab49cc40d9c997be8 | CCn1c(-c2ccccc2)cc2ccccc21.COc1ccccc1C=[N+]1CCCC1>>CCn1c(-c2ccccc2)c(C(c2ccccc2OC)N2CCCC2)c2ccccc21 | C(C)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1.[Cl-].COC1=C(C=[N+]2CCCC2)C=CC=C1>>C(C)N1C(=C(C2=CC=CC=C12)C(N1CCCC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1 | [CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]12.[CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[O:19][CH3:20])=[N+:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH:12]([c:13]2[cH:14... | CCn1c(-c2ccccc2)cc2ccccc21.COc1ccccc1C=[N+]1CCCC1 | CCn1c(-c2ccccc2)c(C(c2ccccc2OC)N2CCCC2)c2ccccc21 | null | null | null | C-C Coupling | OtherReaction | d9d0c5bf4fd4ce1384bf9b4ff949b67b0d13d4469f030dfb035f0b60a70cd412 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-c2[nH]c3ccccc3c2C(c2ccccc2)N2CCCC2)cc1 | [C:1]-[#7;a:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:1-[c:9].[c:10]:[c:11](-[CH;D2;+0:12]=[N+;H0;D3:13]1-[C:14]-[C:15]-[C:16]-[C:17]-1):[c:18]>>[C:1]-[#7;a:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](-[CH;D3;+0:12](-[N;H0;D3;+0:13]2-[C:14]-[C:15]-[C:16]-[C:17]-2)-[c:11](:[c:10]):[c:18]):[c:8]:1-[c:9] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethyl-2-phenyl-1H-indole and 1-(2-methoxy-benzylidene)-pyrrolidinium chloride, which had been prepared in accordance with example 24.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2ccccc2[nH]1.C1CC[NH+]C1 | C1CC[NH]C1.c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1cc2ccccc2[nH]1 | null | null | null | null | CCn1c(-c2ccccc2)cc2ccccc21.COc1ccccc1C=[N+]1CCCC1>>CCn1c(-c2ccccc2)c(C(c2ccccc2OC)N2CCCC2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0332ce0078e14a6cb5e4f7cd2e1699f0 | Cc1ccccc1C=[N+]1CCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>Cc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCC1 | C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1.[Cl-].CC1=C(C=[N+]2CCCC2)C=CC=C1>>C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1C(C1=C(C=CC=C1)C)N1CCCC1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1.[cH:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([c:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[nH:17][c... | Cc1ccccc1C=[N+]1CCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1 | Cc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCC1 | null | null | null | C-C Coupling | OtherReaction | f10e98347794f917e6ce1cf9fd91f6d2dc88458064d6cff7731182da0fa2e5ee | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-c2[nH]c3ccccc3c2C(c2ccccc2)N2CCCC2)cc1 | [c:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:1.[c:9]:[c:10](-[CH;D2;+0:11]=[N+;H0;D3:12]1-[C:13]-[C:14]-[C:15]-[C:16]-1):[c:17]>>[c:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]:1-[CH;D3;+0:11](-[N;H0;D3;+0:12]1-[C:13]-[C:14]-[C:15]-[C:16]-1)-[c:10](:[c:9]):[c:17] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-phenyl-1H-indole and 1-(2-methyl-benzylidene)-pyrrolidinium chloride, which had been prepared in accordance with example 25.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 2... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]C1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]C1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | null | null | null | null | Cc1ccccc1C=[N+]1CCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>Cc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-00adf1ba992d4cb99f816842b438f344 | C1CCNCC1.CC(=O)Cl.Cc1ccccc1C=O>>Cc1ccccc1C=[N+]1CCCCC1.[Cl-] | C(C)(=O)Cl.N1CCCCC1.CC1=C(C=O)C=CC=C1>>[Cl-].CC1=C(C=[N+]2CCCCC2)C=CC=C1 | [NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1.CC(=O)[Cl:15].O=[CH:8][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1.[Cl-:15] | C1CCNCC1.CC(=O)Cl.Cc1ccccc1C=O | Cc1ccccc1C=[N+]1CCCCC1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | faf4b88da581351d4769fed76c5dc27494cac21b814d3867cba4e9d5df33e907 | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | C(c1ccccc1)=[N+]1CCCCC1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N+;H0;D3:8](=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5])-[C:9]-[C:10].[Cl-;H0;D0:1] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 9.5 ml (0.096 mol) piperidine and 4.7 ml (0.040 mol) 2-methylbenzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 2.4 ml (0.040 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 5.8 g (corresponding to 65% of the yield calculated by th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | C1CCNCC1 | C1CC[NH+]CC1 | c1ccccc1.C1CC[NH+]CC1 | HO- | null | null | null | C1CCNCC1.CC(=O)Cl.Cc1ccccc1C=O>>Cc1ccccc1C=[N+]1CCCCC1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-597359ad5d8d4774b20427c336c03943 | Cc1ccccc1C=[N+]1CCCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>Cc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCCC1 | C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1.[Cl-].CC1=C(C=[N+]2CCCCC2)C=CC=C1>>C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1C(C1=C(C=CC=C1)C)N1CCCCC1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1.[cH:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([c:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[... | Cc1ccccc1C=[N+]1CCCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1 | Cc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 35d0198edf0583aaec2ccdd213836154b2c9c1dbce41f0618dd0d8ea42419594 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-c2[nH]c3ccccc3c2C(c2ccccc2)N2CCCCC2)cc1 | [C:1]-[C:2]-[N+;H0;D3:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8]-[C:9].[c:10]-[c:11]1:[#7;a:12]:[c:13](:[c:14]):[c:15](:[c:16]):[cH;D2;+0:17]:1>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:17]1:[c:11](-[c:10]):[#7;a:12]:[c:13](:[c:14]):[c:15]:1:[c:16])-[C:8]-[C:9] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-phenyl-1H-indole and 1-(2-methyl-benzylidene)-piperidinium chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]CC1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | null | null | null | null | Cc1ccccc1C=[N+]1CCCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>Cc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e753da79418a45e58eb565e7c3d4e2a9 | Clc1ccccc1C=[N+]1CCCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>Clc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCCC1 | C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1.[Cl-].ClC1=C(C=[N+]2CCCCC2)C=CC=C1>>ClC1=C(C=CC=C1)C(C1=C(NC2=CC=CC=C12)C1=CC=CC=C1)N1CCCCC1 | [Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1.[cH:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([c:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[nH... | Clc1ccccc1C=[N+]1CCCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1 | Clc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 35d0198edf0583aaec2ccdd213836154b2c9c1dbce41f0618dd0d8ea42419594 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-c2[nH]c3ccccc3c2C(c2ccccc2)N2CCCCC2)cc1 | [C:1]-[C:2]-[N+;H0;D3:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8]-[C:9].[c:10]-[c:11]1:[#7;a:12]:[c:13](:[c:14]):[c:15](:[c:16]):[cH;D2;+0:17]:1>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:17]1:[c:11](-[c:10]):[#7;a:12]:[c:13](:[c:14]):[c:15]:1:[c:16])-[C:8]-[C:9] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-phenyl-1H-indole and 1-(2-chloro-benzylidene)-piperidinium chloride, which had been prepared in accordance with example 26.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 26 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]CC1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | null | null | null | null | Clc1ccccc1C=[N+]1CCCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>Clc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d6a01b849784a7f99927f8025b4abe7 | CC(=O)Cl.CNC.Cc1ccccc1C=O>>Cc1ccccc1C=[N+](C)C.[Cl-] | C(C)(=O)Cl.CNC.CC1=C(C=O)C=CC=C1>>[Cl-].C[N+](=CC1=C(C=CC=C1)C)C | CC(=O)[Cl:12].[NH:9]([CH3:10])[CH3:11].O=[CH:8][c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:9]([CH3:10])[CH3:11].[Cl-:12] | CC(=O)Cl.CNC.Cc1ccccc1C=O | Cc1ccccc1C=[N+](C)C.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | eff493add1f06df45aca8c74a1021d505d12a8600cde1bb3b6b0975b8d046526 | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | c1ccccc1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N+;H0;D3:7](-[C;D1;H3:8])=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[Cl-;H0;D0:1] | 73 | [{"value": 73.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 14.0 ml (0.108 mol) dimethylamine solution and 4.6 ml (0.040 mol) 2-methylbenzaldehyde in accordance with general synthesis instructions 1 and subsequent reaction with 2.4 ml (0.040 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 5.3 g (corresponding to 73% of the yield cal... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)Cl.CNC.Cc1ccccc1C=O>>Cc1ccccc1C=[N+](C)C.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb1b67dc7287425b861bd5d0ec31559a | Cc1ccccc1C=[N+](C)C.c1ccc(-c2cc3ccccc3[nH]2)cc1>>Cc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N(C)C | C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1.[Cl-].C[N+](=CC1=C(C=CC=C1)C)C>>CN(C(C1=C(C=CC=C1)C)C1=C(NC2=CC=CC=C12)C1=CC=CC=C1)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:24]([CH3:25])[CH3:26].[cH:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([c:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[nH:17][c:18]2[cH:19][cH:... | Cc1ccccc1C=[N+](C)C.c1ccc(-c2cc3ccccc3[nH]2)cc1 | Cc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N(C)C | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:15]1:[c:9](-[c:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-phenyl-1H-indole and dimethyl-(2-methyl-benzylidene)-ammonium chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | Cc1ccccc1C=[N+](C)C.c1ccc(-c2cc3ccccc3[nH]2)cc1>>Cc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0540e9ceb8d246e89cbdfe0484553734 | COc1ccccc1C=[N+]1CCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>COc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCC1 | C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1.[Cl-].COC1=C(C=[N+]2CCCC2)C=CC=C1>>COC1=C(C=CC=C1)C(C1=C(NC2=CC=CC=C12)C1=CC=CC=C1)N1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1.[cH:10]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[nH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([c:10]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17... | COc1ccccc1C=[N+]1CCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1 | COc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCC1 | null | null | null | C-C Coupling | OtherReaction | f10e98347794f917e6ce1cf9fd91f6d2dc88458064d6cff7731182da0fa2e5ee | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-c2[nH]c3ccccc3c2C(c2ccccc2)N2CCCC2)cc1 | [c:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:1.[c:9]:[c:10](-[CH;D2;+0:11]=[N+;H0;D3:12]1-[C:13]-[C:14]-[C:15]-[C:16]-1):[c:17]>>[c:1]-[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]:1-[CH;D3;+0:11](-[N;H0;D3;+0:12]1-[C:13]-[C:14]-[C:15]-[C:16]-1)-[c:10](:[c:9]):[c:17] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-phenyl-1H-indole and 1-(2-methoxy-benzylidene)-pyrrolidinium chloride, which had been prepared in accordance with example 24.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]C1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]C1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | null | null | null | null | COc1ccccc1C=[N+]1CCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>COc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-196c1c862b4c4bf289afa7d0c7189a58 | Cc1cccc2[nH]ccc12.Cc1ccccc1C=[N+]1CCCCC1>>Cc1ccccc1C(c1c[nH]c2cccc(C)c12)N1CCCCC1 | CC1=C2C=CNC2=CC=C1.[Cl-].CC1=C(C=[N+]2CCCCC2)C=CC=C1>>CC1=C2C(=CNC2=CC=C1)C(C1=C(C=CC=C1)C)N1CCCCC1 | [cH:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][cH:15][c:16]([CH3:17])[c:18]12.[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([c:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][cH:15][c:16]([CH3:17])[c:18]12)[N:19]1[CH2:20][CH2:21... | Cc1cccc2[nH]ccc12.Cc1ccccc1C=[N+]1CCCCC1 | Cc1ccccc1C(c1c[nH]c2cccc(C)c12)N1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 35d0198edf0583aaec2ccdd213836154b2c9c1dbce41f0618dd0d8ea42419594 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(C(c2c[nH]c3ccccc23)N2CCCCC2)cc1 | [C:1]-[C:2]-[N+;H0;D3:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8]-[C:9].[c:10]:[c:11]1:[#7;a:12]:[c:13]:[cH;D2;+0:14]:[c:15]:1:[c:16]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:14]1:[c:13]:[#7;a:12]:[c:11](:[c:10]):[c:15]:1:[c:16])-[C:8]-[C:9] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-methyl-1H-indole and 1-(2-methyl-benzylidene)-piperidinium chloride, which had been prepared in accordance with example 30.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 30 | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1.C1CC[NH+]CC1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | null | null | null | null | Cc1cccc2[nH]ccc12.Cc1ccccc1C=[N+]1CCCCC1>>Cc1ccccc1C(c1c[nH]c2cccc(C)c12)N1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4711fce3062541c49ba9870e83fae67d | COc1ccccc1C=[N+]1CCCC1.Cc1cccc2[nH]ccc12>>COc1ccccc1C(c1c[nH]c2cccc(C)c12)N1CCCC1 | CC1=C2C=CNC2=CC=C1.[Cl-].COC1=C(C=[N+]2CCCC2)C=CC=C1>>COC1=C(C=CC=C1)C(C1=CNC2=CC=CC(=C12)C)N1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1.[cH:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][cH:16][c:17]([CH3:18])[c:19]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([c:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][cH:16][c:17]([CH3:18])[c:19]12)[N:20]1[CH2:21][CH... | COc1ccccc1C=[N+]1CCCC1.Cc1cccc2[nH]ccc12 | COc1ccccc1C(c1c[nH]c2cccc(C)c12)N1CCCC1 | null | null | null | C-C Coupling | OtherReaction | f10e98347794f917e6ce1cf9fd91f6d2dc88458064d6cff7731182da0fa2e5ee | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(C(c2c[nH]c3ccccc23)N2CCCC2)cc1 | [c:1]:[c:2](-[CH;D2;+0:3]=[N+;H0;D3:4]1-[C:5]-[C:6]-[C:7]-[C:8]-1):[c:9].[c:10]:[c:11]1:[#7;a:12]:[c:13]:[cH;D2;+0:14]:[c:15]:1:[c:16]>>[c:10]:[c:11]1:[#7;a:12]:[c:13]:[c;H0;D3;+0:14](-[CH;D3;+0:3](-[N;H0;D3;+0:4]2-[C:5]-[C:6]-[C:7]-[C:8]-2)-[c:2](:[c:1]):[c:9]):[c:15]:1:[c:16] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-methyl-1H-indole and 1-(2-methoxy-benzylidene)-pyrrolidinium chloride, which had been prepared in accordance with example 24.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]C1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]C1 | c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | null | null | null | null | COc1ccccc1C=[N+]1CCCC1.Cc1cccc2[nH]ccc12>>COc1ccccc1C(c1c[nH]c2cccc(C)c12)N1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8cd12f4f88eb41cca40a2f9a02861d75 | C1CCNCC1.CC(=O)Cl.O=Cc1ccccc1>>C(c1ccccc1)=[N+]1CCCCC1.[Cl-] | C(C)(=O)Cl.N1CCCCC1.C(C1=CC=CC=C1)=O>>[Cl-].C(C1=CC=CC=C1)=[N+]1CCCCC1 | [NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.CC(=O)[Cl:14].O=[CH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1>>[CH:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)=[N+:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.[Cl-:14] | C1CCNCC1.CC(=O)Cl.O=Cc1ccccc1 | C(c1ccccc1)=[N+]1CCCCC1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | faf4b88da581351d4769fed76c5dc27494cac21b814d3867cba4e9d5df33e907 | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | C(c1ccccc1)=[N+]1CCCCC1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N+;H0;D3:8](=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5])-[C:9]-[C:10].[Cl-;H0;D0:1] | 56 | [{"value": 56.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 19.8 ml (0.200 mol) piperidine and 10.1 ml (0.100 mol) benzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 6.0 ml (0.100 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 11.7 g (corresponding to 56% of the yield calculated by theory)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | C1CCNCC1 | C1CC[NH+]CC1 | c1ccccc1.C1CC[NH+]CC1 | HO- | null | null | null | C1CCNCC1.CC(=O)Cl.O=Cc1ccccc1>>C(c1ccccc1)=[N+]1CCCCC1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41e3bdada5244007b94380a43a81235e | C(c1ccccc1)=[N+]1CCCCC1.c1ccc(COc2ccc3[nH]ccc3c2)cc1>>c1ccc(COc2ccc3[nH]cc(C(c4ccccc4)N4CCCCC4)c3c2)cc1 | C(C1=CC=CC=C1)OC=1C=C2C=CNC2=CC1.[Cl-].C(C1=CC=CC=C1)=[N+]1CCCCC1>>C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC1)C(N1CCCCC1)C1=CC=CC=C1 | [CH:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[N+:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]3[nH:11][cH:12][cH:13][c:27]3[cH:28]2)[cH:29][cH:30]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]3[nH:11][cH:12][c:13]([CH:14]([c:15]4[cH... | C(c1ccccc1)=[N+]1CCCCC1.c1ccc(COc2ccc3[nH]ccc3c2)cc1 | c1ccc(COc2ccc3[nH]cc(C(c4ccccc4)N4CCCCC4)c3c2)cc1 | null | null | null | C-C Coupling | OtherReaction | 35d0198edf0583aaec2ccdd213836154b2c9c1dbce41f0618dd0d8ea42419594 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(COc2ccc3[nH]cc(C(c4ccccc4)N4CCCCC4)c3c2)cc1 | [C:1]-[C:2]-[N+;H0;D3:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8]-[C:9].[c:10]:[c:11]1:[cH;D2;+0:12]:[c:13]:[#7;a:14]:[c:15]:1:[c:16]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:12]1:[c:13]:[#7;a:14]:[c:15](:[c:16]):[c:11]:1:[c:10])-[C:8]-[C:9] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-benzyloxy-1H-indole and 1-benzylidene-piperidinium chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]CC1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1.C1CC[NH]CC1 | null | null | null | null | C(c1ccccc1)=[N+]1CCCCC1.c1ccc(COc2ccc3[nH]ccc3c2)cc1>>c1ccc(COc2ccc3[nH]cc(C(c4ccccc4)N4CCCCC4)c3c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-117472a0d67b480f955f6ad22ff17526 | Cc1ccccc1C=[N+](C)C.c1ccc(COc2ccc3[nH]ccc3c2)cc1>>Cc1ccccc1C(c1c[nH]c2ccc(OCc3ccccc3)cc12)N(C)C | C(C1=CC=CC=C1)OC=1C=C2C=CNC2=CC1.[Cl-].C[N+](=CC1=C(C=CC=C1)C)C>>C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC1)C(C1=C(C=CC=C1)C)N(C)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]=[N+:26]([CH3:27])[CH3:28].[cH:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][c:25]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH:8]([c:9]1[cH:10][nH:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]3[... | Cc1ccccc1C=[N+](C)C.c1ccc(COc2ccc3[nH]ccc3c2)cc1 | Cc1ccccc1C(c1c[nH]c2ccc(OCc3ccccc3)cc12)N(C)C | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(COc2ccc3[nH]cc(Cc4ccccc4)c3c2)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-benzyloxy-1H-indole and dimethyl-(2-methyl-benzylidene)-ammonium chloride, which had been prepared in accordance with example 32.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with exam... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | null | null | null | null | Cc1ccccc1C=[N+](C)C.c1ccc(COc2ccc3[nH]ccc3c2)cc1>>Cc1ccccc1C(c1c[nH]c2ccc(OCc3ccccc3)cc12)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-12e6a2521fd3401ea452a00a23616dfb | C1COCCN1.CC(=O)Cl.COc1ccccc1C=O>>COc1ccccc1C=[N+]1CCOCC1.[Cl-] | C(C)(=O)Cl.N1CCOCC1.COC1=C(C=O)C=CC=C1>>[Cl-].COC1=C(C=[N+]2CCOCC2)C=CC=C1 | [NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.CC(=O)[Cl:16].O=[CH:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.[Cl-:16] | C1COCCN1.CC(=O)Cl.COc1ccccc1C=O | COc1ccccc1C=[N+]1CCOCC1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 31879dca4a54a4198f28c09fb4ae420146eea69dd90827d43c74275f7a7a1a1d | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | C(c1ccccc1)=[N+]1CCOCC1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[Cl-;H0;D0:1].[c:4]:[c:3](-[CH;D2;+0:2]=[N+;H0;D3:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:5] | 38 | [{"value": 38.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 18.8 ml (0.216 mol) morpholine and 12.4 g (0.09 mol) 2-methoxybenzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 5.3 ml (0.110 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 7.61 g (corresponding to 38% of the yield calculated by ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | C1COCCN1 | C1COCC[NH+]1 | c1ccccc1.C1COCC[NH+]1 | HO- | null | null | null | C1COCCN1.CC(=O)Cl.COc1ccccc1C=O>>COc1ccccc1C=[N+]1CCOCC1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2d145461bca48b586576fe619b29b95 | CCc1cccc2cc[nH]c12.COc1ccccc1C=[N+]1CCOCC1>>CCc1cccc2c(C(c3ccccc3OC)N3CCOCC3)c[nH]c12 | C(C)C=1C=CC=C2C=CNC12.[Cl-].COC1=C(C=[N+]2CCOCC2)C=CC=C1>>C(C)C=1C=CC=C2C(=CNC12)C(N1CCOCC1)C1=C(C=CC=C1)OC | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:24][nH:25][c:26]12.[CH:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[O:16][CH3:17])=[N+:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[O:16][CH3:17])[N:18]3[CH2:19][CH2... | CCc1cccc2cc[nH]c12.COc1ccccc1C=[N+]1CCOCC1 | CCc1cccc2c(C(c3ccccc3OC)N3CCOCC3)c[nH]c12 | null | null | null | C-C Coupling | OtherReaction | b936d0f8d8fb5adb8b7c960e8e5f394b6777153c7ca8a385ad4d310783595dac | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(C(c2c[nH]c3ccccc23)N2CCOCC2)cc1 | [c:1]:[c:2](-[CH;D2;+0:3]=[N+;H0;D3:4]1-[C:5]-[C:6]-[#8:7]-[C:8]-[C:9]-1):[c:10].[c:11]:[c:12]1:[#7;a:13]:[c:14]:[cH;D2;+0:15]:[c:16]:1:[c:17]>>[c:1]:[c:2](-[CH;D3;+0:3](-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#8:7]-[C:8]-[C:9]-1)-[c;H0;D3;+0:15]1:[c:14]:[#7;a:13]:[c:12](:[c:11]):[c:16]:1:[c:17]):[c:10] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 7-ethyl-1H-indole and 4-(2-methoxy-benzylidene)-morpholin-4-ium chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1.C1COCC[NH+]1 | C1COCC[NH]1.c1ccc2[nH]ccc2c1 | c1ccccc1.C1COCC[NH]1.c1ccc2[nH]ccc2c1 | null | null | null | null | CCc1cccc2cc[nH]c12.COc1ccccc1C=[N+]1CCOCC1>>CCc1cccc2c(C(c3ccccc3OC)N3CCOCC3)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3923885ef3ec4944b51d1b78a332735f | C1CCNCC1.CC(=O)Cl.COc1ccccc1C=O>>COc1ccccc1C=[N+]1CCCCC1.[Cl-] | C(C)(=O)Cl.N1CCCCC1.COC1=C(C=O)C=CC=C1>>[Cl-].COC1=C(C=[N+]2CCCCC2)C=CC=C1 | [NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1.CC(=O)[Cl:16].O=[CH:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1.[Cl-:16] | C1CCNCC1.CC(=O)Cl.COc1ccccc1C=O | COc1ccccc1C=[N+]1CCCCC1.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | faf4b88da581351d4769fed76c5dc27494cac21b814d3867cba4e9d5df33e907 | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | C(c1ccccc1)=[N+]1CCCCC1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N+;H0;D3:8](=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5])-[C:9]-[C:10].[Cl-;H0;D0:1] | 62 | [{"value": 62.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 18.4 g (0.216 mol) piperidine and 25.9 g (0.090 mol) 2-methoxybenzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 5.3 ml (0.11 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 13.4 g (corresponding to 62% of the yield calculated by t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | C1CCNCC1 | C1CC[NH+]CC1 | c1ccccc1.C1CC[NH+]CC1 | HO- | null | null | null | C1CCNCC1.CC(=O)Cl.COc1ccccc1C=O>>COc1ccccc1C=[N+]1CCCCC1.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85dcf7bc766249b39e1ff33b9cbbaf62 | COc1ccccc1C=[N+]1CCCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>COc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCCC1 | C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1.[Cl-].COC1=C(C=[N+]2CCCCC2)C=CC=C1>>COC1=C(C=CC=C1)C(C1=C(NC2=CC=CC=C12)C1=CC=CC=C1)N1CCCCC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1.[cH:10]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[nH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([c:10]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:1... | COc1ccccc1C=[N+]1CCCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1 | COc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 35d0198edf0583aaec2ccdd213836154b2c9c1dbce41f0618dd0d8ea42419594 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(-c2[nH]c3ccccc3c2C(c2ccccc2)N2CCCCC2)cc1 | [C:1]-[C:2]-[N+;H0;D3:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8]-[C:9].[c:10]-[c:11]1:[#7;a:12]:[c:13](:[c:14]):[c:15](:[c:16]):[cH;D2;+0:17]:1>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:17]1:[c:11](-[c:10]):[#7;a:12]:[c:13](:[c:14]):[c:15]:1:[c:16])-[C:8]-[C:9] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-phenyl-1H-indole and 1-(2-methoxy-benzylidene)-piperidinium chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]CC1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | null | null | null | null | COc1ccccc1C=[N+]1CCCCC1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>COc1ccccc1C(c1c(-c2ccccc2)[nH]c2ccccc12)N1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c2eb1b549dd94deb901c071c6cc58834 | COc1ccccc1C=[N+]1CCCCC1.Clc1ccc2[nH]ccc2c1>>COc1ccccc1C(c1c[nH]c2ccc(Cl)cc12)N1CCCCC1 | ClC=1C=C2C=CNC2=CC1.[Cl-].COC1=C(C=[N+]2CCCCC2)C=CC=C1>>ClC=1C=C2C(=CNC2=CC1)C(N1CCCCC1)C1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1.[cH:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([c:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]12)[N:20]1[CH2:... | COc1ccccc1C=[N+]1CCCCC1.Clc1ccc2[nH]ccc2c1 | COc1ccccc1C(c1c[nH]c2ccc(Cl)cc12)N1CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 35d0198edf0583aaec2ccdd213836154b2c9c1dbce41f0618dd0d8ea42419594 | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(C(c2c[nH]c3ccccc23)N2CCCCC2)cc1 | [C:1]-[C:2]-[N+;H0;D3:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8]-[C:9].[c:10]:[c:11]1:[#7;a:12]:[c:13]:[cH;D2;+0:14]:[c:15]:1:[c:16]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:14]1:[c:13]:[#7;a:12]:[c:11](:[c:10]):[c:15]:1:[c:16])-[C:8]-[C:9] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-chloro-1H-indole and 1-(2-methoxy-benzylidene)-piperidinium chloride, which had been prepared in accordance with example 40.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example 4... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]CC1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | null | null | null | null | COc1ccccc1C=[N+]1CCCCC1.Clc1ccc2[nH]ccc2c1>>COc1ccccc1C(c1c[nH]c2ccc(Cl)cc12)N1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-caea7a624f0243c3b2e28a344715d0ec | COc1ccccc1C=[N+]1CCCC1.Clc1ccc2[nH]ccc2c1>>COc1ccccc1C(c1c[nH]c2ccc(Cl)cc12)N1CCCC1 | ClC=1C=C2C=CNC2=CC1.[Cl-].COC1=C(C=[N+]2CCCC2)C=CC=C1>>ClC=1C=C2C(=CNC2=CC1)C(N1CCCC1)C1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1.[cH:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([c:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]12)[N:20]1[CH2:21][CH2:... | COc1ccccc1C=[N+]1CCCC1.Clc1ccc2[nH]ccc2c1 | COc1ccccc1C(c1c[nH]c2ccc(Cl)cc12)N1CCCC1 | null | null | null | C-C Coupling | OtherReaction | f10e98347794f917e6ce1cf9fd91f6d2dc88458064d6cff7731182da0fa2e5ee | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(C(c2c[nH]c3ccccc23)N2CCCC2)cc1 | [c:1]:[c:2](-[CH;D2;+0:3]=[N+;H0;D3:4]1-[C:5]-[C:6]-[C:7]-[C:8]-1):[c:9].[c:10]:[c:11]1:[#7;a:12]:[c:13]:[cH;D2;+0:14]:[c:15]:1:[c:16]>>[c:10]:[c:11]1:[#7;a:12]:[c:13]:[c;H0;D3;+0:14](-[CH;D3;+0:3](-[N;H0;D3;+0:4]2-[C:5]-[C:6]-[C:7]-[C:8]-2)-[c:2](:[c:1]):[c:9]):[c:15]:1:[c:16] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-chloro-1H-indole and 1-(2-methoxy-benzylidene)-pyrrolidinium chloride, which had been prepared in accordance with example 24.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with example ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]C1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]C1 | c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | null | null | null | null | COc1ccccc1C=[N+]1CCCC1.Clc1ccc2[nH]ccc2c1>>COc1ccccc1C(c1c[nH]c2ccc(Cl)cc12)N1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2cc8ecebb78e4dc5bf8438e46e65d6c4 | COc1ccccc1C=[N+]1CCCC1.c1ccc(COc2ccc3[nH]ccc3c2)cc1>>COc1ccccc1C(c1c[nH]c2ccc(OCc3ccccc3)cc12)N1CCCC1 | C(C1=CC=CC=C1)OC=1C=C2C=CNC2=CC1.[Cl-].COC1=C(C=[N+]2CCCC2)C=CC=C1>>C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC1)C(N1CCCC1)C1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1.[cH:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][c:26]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([c:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][... | COc1ccccc1C=[N+]1CCCC1.c1ccc(COc2ccc3[nH]ccc3c2)cc1 | COc1ccccc1C(c1c[nH]c2ccc(OCc3ccccc3)cc12)N1CCCC1 | null | null | null | C-C Coupling | OtherReaction | f10e98347794f917e6ce1cf9fd91f6d2dc88458064d6cff7731182da0fa2e5ee | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(COc2ccc3[nH]cc(C(c4ccccc4)N4CCCC4)c3c2)cc1 | [c:1]:[c:2](-[CH;D2;+0:3]=[N+;H0;D3:4]1-[C:5]-[C:6]-[C:7]-[C:8]-1):[c:9].[c:10]:[c:11]1:[#7;a:12]:[c:13]:[cH;D2;+0:14]:[c:15]:1:[c:16]>>[c:10]:[c:11]1:[#7;a:12]:[c:13]:[c;H0;D3;+0:14](-[CH;D3;+0:3](-[N;H0;D3;+0:4]2-[C:5]-[C:6]-[C:7]-[C:8]-2)-[c:2](:[c:1]):[c:9]):[c:15]:1:[c:16] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 5-benzyloxy-1H-indole and 1-(2-methoxy-benzylidene)-pyrrolidinium chloride, which had been prepared in accordance with example 24.
Conditions: See reaction.notes.procedure_details.
Workup: had been prepared in accordance with examp... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1CC[NH+]C1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.C1CC[NH]C1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1.C1CC[NH]C1 | null | null | null | null | COc1ccccc1C=[N+]1CCCC1.c1ccc(COc2ccc3[nH]ccc3c2)cc1>>COc1ccccc1C(c1c[nH]c2ccc(OCc3ccccc3)cc12)N1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6fc688613ae646f2a32ab26807d5074f | CC(=O)Cl.CNC.COc1ccccc1C=O>>COc1ccccc1C=[N+](C)C.[Cl-] | C(C)(=O)Cl.CNC.COC1=C(C=O)C=CC=C1>>[Cl-].COC1=C(C=[N+](C)C)C=CC=C1 | CC(=O)[Cl:13].[NH:10]([CH3:11])[CH3:12].O=[CH:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:10]([CH3:11])[CH3:12].[Cl-:13] | CC(=O)Cl.CNC.COc1ccccc1C=O | COc1ccccc1C=[N+](C)C.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | eff493add1f06df45aca8c74a1021d505d12a8600cde1bb3b6b0975b8d046526 | fb43ad6d28a8b121285f4adfe8f950669469698aabd83903368c0912f0cf003a | c1ccccc1 | C-C(=O)-[Cl;H0;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N+;H0;D3:7](-[C;D1;H3:8])=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[Cl-;H0;D0:1] | 48 | [{"value": 48.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 17.0 ml (0.135 mol) dimethylamine solution and 6.8 g ml (0.050 mol) 2-methoxybenzaldehyde in accordance with general synthesis instructions 1 and subsequent reaction with 3.0 ml (0.050 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 4.8 g (corresponding to 48% of the yield ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Secondary amine | null | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)Cl.CNC.COc1ccccc1C=O>>COc1ccccc1C=[N+](C)C.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c2c231d55e2b4f149603923349bae181 | COc1ccccc1C=[N+](C)C.Cc1cc2ccccc2[nH]1>>COc1ccccc1C(c1c(C)[nH]c2ccccc12)N(C)C | CC=1NC2=CC=CC=C2C1.[Cl-].COC1=C(C=[N+](C)C)C=CC=C1>>COC1=C(C=CC=C1)C(C1=C(NC2=CC=CC=C12)C)N(C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]=[N+:20]([CH3:21])[CH3:22].[cH:10]1[c:11]([CH3:12])[nH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([c:10]1[c:11]([CH3:12])[nH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12)[N:20]([CH3:21])[CH3:22] | COc1ccccc1C=[N+](C)C.Cc1cc2ccccc2[nH]1 | COc1ccccc1C(c1c(C)[nH]c2ccccc12)N(C)C | null | null | null | C-C Coupling | OtherReaction | 6f78ebae7a6e5f9c15e0d6ab78f58f64a17b670729ecfc39fbb9b9e11c788fae | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1ccc(Cc2c[nH]c3ccccc23)cc1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[CH;D3;+0:4](-[N;H0;D3;+0:2](-[C;D1;H3:1])-[C;D1;H3:3])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methyl-1H-indole and (2-methoxy-benzylidene)-dimethyl-ammonium chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | null | null | null | null | COc1ccccc1C=[N+](C)C.Cc1cc2ccccc2[nH]1>>COc1ccccc1C(c1c(C)[nH]c2ccccc12)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3c81413a8c741a6b51eebe1bb0d4a46 | COc1ccc(CCl)cc1.C[N+](C)=Cc1ccccc1.c1ccc2[nH]ccc2c1>>COc1ccc(Cn2cc(C(c3ccccc3)N(C)C)c3ccccc32)cc1 | N1C=CC2=CC=CC=C12.[Cl-].C(C1=CC=CC=C1)=[N+](C)C.COC1=CC=C(CCl)C=C1>>COC1=CC=C(CN2C=C(C3=CC=CC=C23)C(C2=CC=CC=C2)N(C)C)C=C1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]1.[CH:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[N+:18]([CH3:19])[CH3:20].[nH:8]1[cH:9][cH:10][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][c:10]([CH:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)... | COc1ccc(CCl)cc1.C[N+](C)=Cc1ccccc1.c1ccc2[nH]ccc2c1 | COc1ccc(Cn2cc(C(c3ccccc3)N(C)C)c3ccccc32)cc1 | null | null | null | C-C Coupling | OtherReaction | 33bfdcfcc30dd9084deb8c9b5ab0eba92999012c7a3e96a3ea6c304332de7c1a | 38f76f5ecf3a6ff60bf21a305b5ad50a8eb32355d6b483771e784421fea31a14 | c1ccc(Cc2cn(Cc3ccccc3)c3ccccc23)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[N+;H0;D3:6](-[C;D1;H3:7])=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11].[c:12]:[c:13]1:[cH;D2;+0:14]:[c:15]:[nH;D2;+0:16]:[c:17]:1:[c:18]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:14]1:[c:15]:[n;H0;D3;+0:16](-[CH2;D2;+0:1]-[c:2](:[c... | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 and 5 from 1H-indole, benzylidene-dimethyl-ammonium chloride and 4-methoxybenzyl chloride
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | HCl | null | null | null | COc1ccc(CCl)cc1.C[N+](C)=Cc1ccccc1.c1ccc2[nH]ccc2c1>>COc1ccc(Cn2cc(C(c3ccccc3)N(C)C)c3ccccc32)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07c36c5d800843d9967723d5d67b4e5f | CNC.O=Cc1cc(Br)ccc1F.O=[N+]([O-])c1cccc2[nH]ccc12>>CN(C)C(c1cc(Br)ccc1F)c1c[nH]c2cccc([N+](=O)[O-])c12 | [N+](=O)([O-])C1=C2C=CNC2=CC=C1.[Cl-].BrC=1C=CC(=C(C=[N+](C)C)C1)F.BrC=1C=CC(=C(C=O)C1)F.CNC>>BrC=1C=CC(=C(C1)C(C1=CNC2=CC=CC(=C12)[N+](=O)[O-])N(C)C)F | [CH3:1][NH:2][CH3:3].O=[CH:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[F:12].[cH:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[c:24]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[F:12])[c:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:... | CNC.O=Cc1cc(Br)ccc1F.O=[N+]([O-])c1cccc2[nH]ccc12 | CN(C)C(c1cc(Br)ccc1F)c1c[nH]c2cccc([N+](=O)[O-])c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-nitroindole and (5-bromo-2-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 5-bromo-2-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.O=Cc1cc(Br)ccc1F.O=[N+]([O-])c1cccc2[nH]ccc12>>CN(C)C(c1cc(Br)ccc1F)c1c[nH]c2cccc([N+](=O)[O-])c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-598639165ac04cc8a8c4efb2e52fbbdb | CNC.Cn1ccc2ccccc21.O=Cc1cc(Br)ccc1F>>CN(C)C(c1cc(Br)ccc1F)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].BrC=1C=CC(=C(C=[N+](C)C)C1)F.BrC=1C=CC(=C(C=O)C1)F.CNC>>BrC=1C=CC(=C(C1)C(C1=CN(C2=CC=CC=C12)C)N(C)C)F | [CH3:1][NH:2][CH3:3].[cH:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12.O=[CH:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[F:12]>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[F:12])[c:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | CNC.Cn1ccc2ccccc21.O=Cc1cc(Br)ccc1F | CN(C)C(c1cc(Br)ccc1F)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methylindole and (5-bromo-2-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 5-bromo-2-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CNC.Cn1ccc2ccccc21.O=Cc1cc(Br)ccc1F>>CN(C)C(c1cc(Br)ccc1F)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab06589450384aad9d4c3c244b329c3c | CNC.O=Cc1c(F)cccc1Cl.c1ccc(-c2cc3ccccc3[nH]2)cc1>>CN(C)C(c1c(F)cccc1Cl)c1c(-c2ccccc2)[nH]c2ccccc12 | C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1.[Cl-].ClC1=C(C=[N+](C)C)C(=CC=C1)F.ClC1=C(C=O)C(=CC=C1)F.CNC>>ClC1=C(C(=CC=C1)F)C(C1=C(NC2=CC=CC=C12)C1=CC=CC=C1)N(C)C | [CH3:1][NH:2][CH3:3].O=[CH:4][c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12].[cH:13]1[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[nH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12])[c:13]1[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:... | CNC.O=Cc1c(F)cccc1Cl.c1ccc(-c2cc3ccccc3[nH]2)cc1 | CN(C)C(c1c(F)cccc1Cl)c1c(-c2ccccc2)[nH]c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:15]1:[c:9](-[c:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-phenylindole and (2-chloro-6-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-chloro-6-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.O=Cc1c(F)cccc1Cl.c1ccc(-c2cc3ccccc3[nH]2)cc1>>CN(C)C(c1c(F)cccc1Cl)c1c(-c2ccccc2)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-edbb3ab502d0484fa2274b7010e61a5c | CCn1ccc2ccccc21.CNC.C[N+](C)=Cc1c(F)cccc1Cl.O=Cc1c(F)cccc1Cl>>CCn1c(-c2ccccc2)c(C(c2c(F)cccc2Cl)N(C)C)c2ccccc21 | C(C)N1C=CC2=CC=CC=C12.[Cl-].ClC1=C(C=[N+](C)C)C(=CC=C1)F.ClC1=C(C=O)C(=CC=C1)F.CNC>>ClC1=C(C(=CC=C1)F)C(C1=C(N(C2=CC=CC=C12)CC)C1=CC=CC=C1)N(C)C | [CH3:1][CH2:2][n:3]1[cH:4][cH:11][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]12.[NH:21]([CH3:22])[CH3:23].C[N+](C)=C[c:5]1[c:6](F)[cH:7][cH:8][cH:9][c:10]1Cl.O=[CH:12][c:13]1[c:14]([F:15])[cH:16][cH:17][cH:18][c:19]1[Cl:20]>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH:12]([c:13]2[c:14]([F:... | CCn1ccc2ccccc21.CNC.C[N+](C)=Cc1c(F)cccc1Cl.O=Cc1c(F)cccc1Cl | CCn1c(-c2ccccc2)c(C(c2c(F)cccc2Cl)N(C)C)c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a6d3a66d05cf7c811796b5786de8c7c94c6bba62c5ef58a21f018e2ad57b0cfb | 4219e9fdf45033f4a021c7f1417d93b41d8c482a9f8bb7c8497f5f3dd0f18ab1 | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | C-[N+](-C)=C-[c;H0;D3;+0:1]1:[c;H0;D3;+0:2](-Cl):[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-F.O=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10].[C;D1;H3:11]-[NH;D2;+0:12]-[C;D1;H3:13].[C:14]-[#7;a:15]1:[cH;D2;+0:16]:[cH;D2;+0:17]:[c:18](:[c:19]):[c:20]:1:[c:21]>>[C:14]-[#7;a:15]1:[c:20](:[c:21]):[c:18](:[c:19]):[c;H0;D3;+0:17](-[CH;D3;+0:7]... | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethylindole and (2-chloro-6-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-chloro-6-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | HF | null | null | null | CCn1ccc2ccccc21.CNC.C[N+](C)=Cc1c(F)cccc1Cl.O=Cc1c(F)cccc1Cl>>CCn1c(-c2ccccc2)c(C(c2c(F)cccc2Cl)N(C)C)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e7fd6d13f8044488ab16986845c5eb8 | CNC.O=Cc1c(F)cccc1Cl.O=[N+]([O-])c1cccc2[nH]ccc12>>CN(C)C(c1c(F)cccc1Cl)c1c[nH]c2cccc([N+](=O)[O-])c12 | [N+](=O)([O-])C1=C2C=CNC2=CC=C1.[Cl-].ClC1=C(C=[N+](C)C)C(=CC=C1)F.ClC1=C(C=O)C(=CC=C1)F.CNC>>ClC1=C(C(=CC=C1)F)C(C1=CNC2=CC=CC(=C12)[N+](=O)[O-])N(C)C | [CH3:1][NH:2][CH3:3].O=[CH:4][c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12].[cH:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[c:24]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12])[c:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:... | CNC.O=Cc1c(F)cccc1Cl.O=[N+]([O-])c1cccc2[nH]ccc12 | CN(C)C(c1c(F)cccc1Cl)c1c[nH]c2cccc([N+](=O)[O-])c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-nitroindole and (2-chloro-6-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-chloro-6-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CNC.O=Cc1c(F)cccc1Cl.O=[N+]([O-])c1cccc2[nH]ccc12>>CN(C)C(c1c(F)cccc1Cl)c1c[nH]c2cccc([N+](=O)[O-])c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7345c951d05470292bcb46ef9aae0f4 | CNC.Cn1ccc2ccccc21.O=Cc1c(F)cccc1Cl>>CN(C)C(c1c(F)cccc1Cl)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].ClC1=C(C=[N+](C)C)C(=CC=C1)F.ClC1=C(C=O)C(=CC=C1)F.CNC>>ClC1=C(C(=CC=C1)F)C(C1=CN(C2=CC=CC=C12)C)N(C)C | [CH3:1][NH:2][CH3:3].[cH:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12.O=[CH:4][c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12]>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12])[c:13]1[cH:14][n:15]([CH3:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | CNC.Cn1ccc2ccccc21.O=Cc1c(F)cccc1Cl | CN(C)C(c1c(F)cccc1Cl)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methylindole and (2-chloro-6-fluoro-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-chloro-6-fluoro-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CNC.Cn1ccc2ccccc21.O=Cc1c(F)cccc1Cl>>CN(C)C(c1c(F)cccc1Cl)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e8efe4c9dd34c7aac52fa7a5a546e0f | CNC.C[N+](C)=Cc1ccccc1Br.O=[N+]([O-])c1cccc2[nH]ccc12>>CN(C)C(c1ccccc1Br)c1c[nH]c2cccc([N+](=O)[O-])c12 | [N+](=O)([O-])C1=C2C=CNC2=CC=C1.[Cl-].BrC1=C(C=[N+](C)C)C=CC=C1.BrC1=C(C=O)C=CC=C1.CNC>>BrC1=C(C=CC=C1)C(C1=CNC2=CC=CC(=C12)[N+](=O)[O-])N(C)C | [CH3:1][NH:2][CH3:3].C[N+](C)=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11].[cH:12]1[cH:13][nH:14][c:15]2[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[c:23]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11])[c:12]1[cH:13][nH:14][c:15]2[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[O-... | CNC.C[N+](C)=Cc1ccccc1Br.O=[N+]([O-])c1cccc2[nH]ccc12 | CN(C)C(c1ccccc1Br)c1c[nH]c2cccc([N+](=O)[O-])c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4aae3a4ea1be485aab9d544da9fceb1ce060e1d3dd462597adbb05c8cde19188 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(Cc2c[nH]c3ccccc23)cc1 | C-[N+](-C)=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 4-nitroindole and (2-bromo-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-bromo-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | null | null | null | CNC.C[N+](C)=Cc1ccccc1Br.O=[N+]([O-])c1cccc2[nH]ccc12>>CN(C)C(c1ccccc1Br)c1c[nH]c2cccc([N+](=O)[O-])c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43a1006b592240de9f9ea762bf1dffbe | CNC.Cn1ccc2ccccc21.O=Cc1ccccc1Br>>CN(C)C(c1ccccc1Br)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].BrC1=C(C=[N+](C)C)C=CC=C1.BrC1=C(C=O)C=CC=C1.CNC>>BrC1=C(C=CC=C1)C(C1=CN(C2=CC=CC=C12)C)N(C)C | [CH3:1][NH:2][CH3:3].[cH:12]1[cH:13][n:14]([CH3:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11]>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11])[c:12]1[cH:13][n:14]([CH3:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | CNC.Cn1ccc2ccccc21.O=Cc1ccccc1Br | CN(C)C(c1ccccc1Br)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methylindole and (2-bromo-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 2-bromo-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CNC.Cn1ccc2ccccc21.O=Cc1ccccc1Br>>CN(C)C(c1ccccc1Br)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b9dbd5da2cdd4c458aca2c317f2b4bc7 | CCc1cccc2cc[nH]c12.CNC.O=Cc1cccc(Br)c1>>CCc1cccc2c(C(c3cccc(Br)c3)N(C)C)c[nH]c12 | C(C)C=1C=CC=C2C=CNC12.[Cl-].BrC=1C=C(C=[N+](C)C)C=CC1.BrC=1C=C(C=O)C=CC1.CNC>>BrC=1C=C(C=CC1)C(C1=CNC2=C(C=CC=C12)CC)N(C)C | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:20][nH:21][c:22]12.[NH:17]([CH3:18])[CH3:19].O=[CH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([Br:15])[cH:16]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([CH:9]([c:10]3[cH:11][cH:12][cH:13][c:14]([Br:15])[cH:16]3)[N:17]([CH3:18])[CH3:19])[cH:20][nH:21][c:22]12 | CCc1cccc2cc[nH]c12.CNC.O=Cc1cccc(Br)c1 | CCc1cccc2c(C(c3cccc(Br)c3)N(C)C)c[nH]c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 7-ethylindole and (3-bromo-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 3-bromo-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CCc1cccc2cc[nH]c12.CNC.O=Cc1cccc(Br)c1>>CCc1cccc2c(C(c3cccc(Br)c3)N(C)C)c[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b13a6bf96a74499cb0f5ac0624c03e7c | CNC.Cn1ccc2ccccc21.O=Cc1cccc(Br)c1>>CN(C)C(c1cccc(Br)c1)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].BrC=1C=C(C=[N+](C)C)C=CC1.BrC=1C=C(C=O)C=CC1.CNC>>BrC=1C=C(C=CC1)C(C1=CN(C2=CC=CC=C12)C)N(C)C | [CH3:1][NH:2][CH3:3].[cH:12]1[cH:13][n:14]([CH3:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1)[c:12]1[cH:13][n:14]([CH3:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | CNC.Cn1ccc2ccccc21.O=Cc1cccc(Br)c1 | CN(C)C(c1cccc(Br)c1)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methylindole and (3-bromo-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 3-bromo-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CNC.Cn1ccc2ccccc21.O=Cc1cccc(Br)c1>>CN(C)C(c1cccc(Br)c1)c1cn(C)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9713eb6bb86a4e5b8e91f5c6e222090d | CC(C)(C)c1ccc(C=O)cc1.CNC.Cc1cc2ccccc2[nH]1>>Cc1[nH]c2ccccc2c1C(c1ccc(C(C)(C)C)cc1)N(C)C | CC=1NC2=CC=CC=C2C1.[Cl-].C(C)(C)(C)C1=CC=C(C=[N+](C)C)C=C1.C(C)(C)(C)C1=CC=C(C=O)C=C1.CNC>>C(C)(C)(C)C1=CC=C(C=C1)C(C1=C(NC2=CC=CC=C12)C)N(C)C | O=[CH:11][c:12]1[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]1.[NH:22]([CH3:23])[CH3:24].[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[cH:10]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]1[CH:11]([c:12]1[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][... | CC(C)(C)c1ccc(C=O)cc1.CNC.Cc1cc2ccccc2[nH]1 | Cc1[nH]c2ccccc2c1C(c1ccc(C(C)(C)C)cc1)N(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1e887ffc9d31747076f97173ff8dc6f44b0480e2cfa9f6a88ab0a775ac92e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[cH;D2;+0:15]:1>>[C;D1;H3:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15]:1-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 2-methylindole and (4-tert-butyl-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 4-tert-butyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | CC(C)(C)c1ccc(C=O)cc1.CNC.Cc1cc2ccccc2[nH]1>>Cc1[nH]c2ccccc2c1C(c1ccc(C(C)(C)C)cc1)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f5670550e504409380546e6e65149d0e | CC(C)(C)c1ccc(C=O)cc1.CCn1c(-c2ccccc2)cc2ccccc21.CNC>>CCn1c(-c2ccccc2)c(C(c2ccc(C(C)(C)C)cc2)N(C)C)c2ccccc21 | C(C)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1.[Cl-].C(C)(C)(C)C1=CC=C(C=[N+](C)C)C=C1.C(C)(C)(C)C1=CC=C(C=O)C=C1.CNC>>C(C)(C)(C)C1=CC=C(C=C1)C(C1=C(N(C2=CC=CC=C12)CC)C1=CC=CC=C1)N(C)C | O=[CH:12][c:13]1[cH:14][cH:15][c:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22]1.[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]12.[NH:23]([CH3:24])[CH3:25]>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]([CH:12]([c:13]2... | CC(C)(C)c1ccc(C=O)cc1.CCn1c(-c2ccccc2)cc2ccccc21.CNC | CCn1c(-c2ccccc2)c(C(c2ccc(C(C)(C)C)cc2)N(C)C)c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bec24864ceecfec904d98640b3bb3caa9d35fa656dcbdac3c55c0dacb43b50eb | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c(-c3ccccc3)[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7].[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:1-[c:16]>>[C:8]-[#7;a:9]1:[c:10](:[c:11]):[c:12](:[c:13]):[c;H0;D3;+0:14](-[CH;D3;+0:1](-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7])-[c:2](:[c:3]):[c:4]):[c:15]:1-[c:16] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-ethyl-2-phenylindole and (4-tert-butyl-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 4-tert-butyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | HO- | null | null | null | CC(C)(C)c1ccc(C=O)cc1.CCn1c(-c2ccccc2)cc2ccccc21.CNC>>CCn1c(-c2ccccc2)c(C(c2ccc(C(C)(C)C)cc2)N(C)C)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cd3d1d7842614bdcaa46121f99044cdb | CC(C)(C)c1ccc(C=O)cc1.CNC.Cn1ccc2ccccc21>>CN(C)C(c1ccc(C(C)(C)C)cc1)c1cn(C)c2ccccc12 | CN1C=CC2=CC=CC=C12.[Cl-].C(C)(C)(C)C1=CC=C(C=[N+](C)C)C=C1.C(C)(C)(C)C1=CC=C(C=O)C=C1.CNC>>C(C)(C)(C)C1=CC=C(C=C1)C(C1=CN(C2=CC=CC=C12)C)N(C)C | O=[CH:4][c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14]1.[CH3:1][NH:2][CH3:3].[cH:15]1[cH:16][n:17]([CH3:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][N:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14]1)[c:15]1[cH:16][n:17]([CH3:18])[c:19]2[c... | CC(C)(C)c1ccc(C=O)cc1.CNC.Cn1ccc2ccccc21 | CN(C)C(c1ccc(C(C)(C)C)cc1)c1cn(C)c2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 05894bd812613f52cf9c1620f3154e6ca08db53b10e13d8864b239f8fa88e3d5 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(Cc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12].[C;D1;H3:13]-[NH;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[CH;D3;+0:1](-[N;H0;D3;+0:14](-[C;D1;H3:13])-[C;D1;H3:15])-[c:2](:[c:3]):[c:4]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The preparation was carried out in accordance with general synthesis instructions 4 from 1-methylindole and (4-tert-butyl-benzylidene)-dimethyl-ammonium chloride, which had been prepared in accordance with example 24 from 4-tert-butyl-benzaldehyde and dimethylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | HO- | null | null | null | CC(C)(C)c1ccc(C=O)cc1.CNC.Cn1ccc2ccccc21>>CN(C)C(c1ccc(C(C)(C)C)cc1)c1cn(C)c2ccccc12 |
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