dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0bbaa1dd2d284674aff4b80eef62d499 | CCOC(=O)/C=C/C(=O)c1ccccc1.C[C@H](N)C(=O)[O-]>>CCOC(=O)C(CC(=O)c1ccccc1)N[C@@H](C)C(=O)O | C(C1=CC=CC=C1)(=O)/C=C/C(=O)OCC.[Li+].N[C@@H](C)C(=O)[O-].Cl>>C(C)OC(=O)C(CC(C1=CC=CC=C1)=O)N[C@@H](C)C(=O)O | [CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[NH2:16][C@@H:17]([CH3:18])[C:19](=[O:20])[O-:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[NH:16][C@@H:17]([CH3:18])[C:19](=[O:20])[OH:21] | CCOC(=O)/C=C/C(=O)c1ccccc1.C[C@H](N)C(=O)[O-] | CCOC(=O)C(CC(=O)c1ccccc1)N[C@@H](C)C(=O)O | null | C(C)OC(=O)[C@H](CC(C1=CC=CC=C1)=O)N[C@@H](C)C(=O)O | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | a48db627b1a60a2e706f470f93d19b40adaa674f71e142fd0727c884ede4a46e | 9a89855d935cfe41028ca5beb7f769ba2290e664dd336f04443f94e0f5c7a7e1 | c1ccccc1 | [C;D1;H3:1]-[C:2](-[NH2;D1;+0:3])-[C:4](-[O-;H0;D1:5])=[O;D1;H0:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])/[CH;D2;+0:11]=[CH;D2;+0:12]/[C:13](=[O;D1;H0:14])-[c:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[CH2;D2;+0:12]-[C:13](=[O;D1;H0:14])-[c:15])-[NH;D2;+0:3]-[C:2](-[C;D1;H3:1])-[C:4](=[O;D1;H0:6])-[OH;D1;+0:5] | 68.2 | [{"value": 68.2, "product": "C(C)OC(=O)C(CC(C1=CC=CC=C1)=O)N[C@@H](C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 25.9 g of ethyl trans-β-benzoylacrylate in 770 ml of ethanol was added a solution of 6.03 g of L-alanine lithium salt in 426 ml of ethanol over 30 minutes at room temperature. After completion of addition, the mixture was stirred for an additional 5 minutes, and then 5.29 ml of concentrated hydrochlori... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Carboxylic acid.Ketone.Ester.Secondary amine | null | null | c1ccccc1 | null | C(C)OC(=O)[C@H](CC(C1=CC=CC=C1)=O)N[C@@H](C)C(=O)O.C(C)O | null | 0.083333 | CCOC(=O)/C=C/C(=O)c1ccccc1.C[C@H](N)C(=O)[O-]>C(C)OC(=O)[C@H](CC(C1=CC=CC=C1)=O)N[C@@H](C)C(=O)O.C(C)O>CCOC(=O)C(CC(=O)c1ccccc1)N[C@@H](C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-22128d0e18414868bd6ebb4b112f1466 | N.O=C(O)CC(O)C(=O)O>>N[C@@H](CC(=O)O)C(=O)O | C(C(O)CC(=O)[O-])(=O)[O-].[Na+].[Na+].N.C(C(O)CC(=O)O)(=O)O>>N[C@@H](CC(=O)O)C(=O)O | [NH3:1].O[CH:2]([CH2:3][C:4](=[O:5])[OH:6])[C:7](=[O:8])[OH:9]>>[NH2:1][C@@H:2]([CH2:3][C:4](=[O:5])[OH:6])[C:7](=[O:8])[OH:9] | N.O=C(O)CC(O)C(=O)O | N[C@@H](CC(=O)O)C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 9451e62ed261b338129e937dd880a3da1bfb44bef893cf7f13d5f6787cc78439 | ecf4f748a9ad63b7cccc0f035fcddcd3d49bbf43f6eeb22a08e8c42ae1aa114b | null | O-[CH;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].[NH3;D0;+0:9]>>[NH2;D1;+0:9]-[C@@H;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | null | [] | null | null | 0.181 | SECOND | The concentrations of the substrates prior to entering the reactor were 0.168 M for sodium malate and 1.797 M for aqueous ammonia. The reaction time was 0.181 second, and the aqueous solution obtained after the reaction was examined with a high performance liquid chromatography/mass spectroscopy apparatus, which confir... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Primary amine | null | null | null | HO- | null | null | 0.00005 | N.O=C(O)CC(O)C(=O)O>>N[C@@H](CC(=O)O)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-300070830e1d40019e62ab5969babd71 | CCOC(=O)CC(C)O.N>>CCOC(=O)CC(C)N | OC(CC(=O)OCC)C.N.OC(CC(=O)OCC)C>>NC(CC(=O)OCC)C | O[CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:8].[NH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([CH3:8])[NH2:9] | CCOC(=O)CC(C)O.N | CCOC(=O)CC(C)N | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 9451e62ed261b338129e937dd880a3da1bfb44bef893cf7f13d5f6787cc78439 | ecf4f748a9ad63b7cccc0f035fcddcd3d49bbf43f6eeb22a08e8c42ae1aa114b | null | O-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[NH3;D0;+0:8]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH2;D1;+0:8] | null | [] | null | null | 0.201 | SECOND | The concentrations of the substrates prior to entering the reactor were 0.226 M for ethyl 3-hydroxy-n-butyrate and 1.630 M for aqueous ammonia. The reaction time was 0.201 second, and the aqueous solution obtained after the reaction was examined with a high performance liquid chromatography/mass spectroscopy apparatus,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Primary amine | null | null | null | HO- | null | null | 0.000056 | CCOC(=O)CC(C)O.N>>CCOC(=O)CC(C)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a072c99a12e14176be1d8341ca062ead | C=C(C)C(=O)O.C=CC(=O)O.CC1(O)C2CC3CC(C2)CC1C3>>C=C(C)C(=O)OC1(C)C2CC3CC(C2)CC1C3.C=CC(=O)OC1(C)C2CC3CC(C2)CC1C3 | C(C(=C)C)(=O)O.C(C=C)(=O)O.CC1(C2CC3CC(CC1C3)C2)O>>C(C=C)(=O)OC1(C2CC3CC(CC1C3)C2)C.C(C(=C)C)(=O)OC1(C2CC3CC(CC1C3)C2)C | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[OH:6].O[C:20]([CH:19]=[CH2:18])=[O:21].[CH2:7]1[CH:25]2[C:23]([OH:22])([CH3:24])[CH:32]3[CH2:31][CH:29]([CH2:28][CH:27]1[CH2:33]3)[CH2:30]2>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][C:7]1([CH3:8])[CH:9]2[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14]2)[CH2:15][CH:16]1[CH2:17]3.[CH2:18]=[CH:... | C=C(C)C(=O)O.C=CC(=O)O.CC1(O)C2CC3CC(C2)CC1C3 | C=C(C)C(=O)OC1(C)C2CC3CC(C2)CC1C3.C=CC(=O)OC1(C)C2CC3CC(C2)CC1C3 | null | null | null | C-C Coupling | OtherReaction | cf8a846749d94fda1670fafb7740599a6b17295a8b0f6f1ad365cd0157daf308 | 52b8c1c3054f1b60e77192633b4376f56206f00ba087210ec56150e15e52fe8c | C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C;D1;H2:5]=[C:6](-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10].[C;D1;H3:11]-[C:12]1(-[OH;D1;+0:13])-[C:14]-[C:15]-[CH;D3;+0:16]2-[C:17]-[C:18]-[C:19]-[CH;D3;+0:20]-1-[CH2;D2;+0:21]-2>>[C;D1;H2:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:13]-[C:12]1(-[C;D1;H3:11]... | null | [] | null | null | null | null | For example, by conducting a reaction using, as the 2-alkyl-2-adamantanol, 2-methyl-2-adamantanol and, as the carboxylic acid compound, acrylic acid or methacrylic acid, there is obtained 2-methyl-2-adamantyl acrylate or 2-methyl-2-adamantyl methacrylate.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Tertiary alcohol | Ester.Ester | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3 | null | null | null | null | C=C(C)C(=O)O.C=CC(=O)O.CC1(O)C2CC3CC(C2)CC1C3>>C=C(C)C(=O)OC1(C)C2CC3CC(C2)CC1C3.C=CC(=O)OC1(C)C2CC3CC(C2)CC1C3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-027d4c7cc0c844d4951bbb55fc5019b0 | O=C1C2CC3CC(C2)CC1C3.[CH3][Mg][Br]>>CC1(O)C2CC3CC(C2)CC1C3.[Br-].[Br-].[Mg+2] | C[Mg]Br.C12C(C3CC(CC(C1)C3)C2)=O.[Cl-].[Ca+2].[Cl-]>>[Br-].[Mg+2].[Br-].CC1(C2CC3CC(CC1C3)C2)O | [C:2]1(=[O:3])[CH:4]2[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9]2)[CH2:10][CH:11]1[CH2:12]3.[CH3:1][Mg:15][Br:13]>>[CH3:1][C:2]1([OH:3])[CH:4]2[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9]2)[CH2:10][CH:11]1[CH2:12]3.[Br-:13].[Br-:14].[Mg+2:15] | O=C1C2CC3CC(C2)CC1C3.[CH3][Mg][Br] | CC1(O)C2CC3CC(C2)CC1C3.[Br-].[Br-].[Mg+2] | null | null | O1CCCC1 | C-C Coupling | Grignard from ketone to alcohol | de58e3578bcabaa8130cdb1293e3d1198486c5597bf3c3f014abf924310e22d2 | 5854166cd4ea706bc07d74dc79eb8f4a990bc6c5eacbf0ca947d88ee86e78fdf | C1C2CC3CC1CC(C2)C3 | [Br;H0;D1;+0:1]-[Mg;H0;D2;+0:2]-[CH3;D1;+0:3].[C:4]-[C:5](-[C:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9](-[C:10])-[C:11]>>[Br-;H0;D0:1].[C:4]-[C:5](-[C:6])-[C;H0;D4;+0:7](-[CH3;D1;+0:3])(-[OH;D1;+0:8])-[C:9](-[C:10])-[C:11].[Mg+2;H0;D0:2] | null | [] | 50 | CELSIUS | 3 | HOUR | 44 ml of a tetrahydrofuran solution containing 0.06 mole of methyl magnesium bromide was added into a 200-ml four-necked flask provided with a stirrer and a drying tube filled with calcium chloride. There to was dropwise added, at room temperature in a nitrogen atmosphere, a solution of 7.5 g (0.05 mole) of 2-adamantan... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Tertiary alcohol | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | null | O1CCCC1 | 50 | 3 | O=C1C2CC3CC(C2)CC1C3.[CH3][Mg][Br]>O1CCCC1>CC1(O)C2CC3CC(C2)CC1C3.[Br-].[Br-].[Mg+2] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9e3ab67d169346afb69f5d801a2c7a3e | C=C(C)C(=O)OC1(C)C2CC3CC(C2)CC1C3>>C=C1C2CC3CC(C2)CC1C3 | C12(CC3CC(CC(C1)C3)C2)O.S(=O)(=O)([O-])[O-].[Mg+2].C(C(=C)C)(=O)OC1(C2CC3CC(CC1C3)C2)C>>C=C1C2CC3CC(CC1C3)C2 | CC1(OC(=O)[C:2](C)=[CH2:1])[CH:3]2[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8]2)[CH2:9][CH:10]1[CH2:11]3>>[CH2:1]=[C:2]1[CH:3]2[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8]2)[CH2:9][CH:10]1[CH2:11]3 | C=C(C)C(=O)OC1(C)C2CC3CC(C2)CC1C3 | C=C1C2CC3CC(C2)CC1C3 | null | null | CCCCCC | Miscellaneous | OtherReaction | 5ea5b19943d8b1c261c5bacb62a7de2fe8569047fe5c3a8ac9fe076483f89cf5 | efa4a3eda18860b9357d027555cb83dfb201db6d609465b9676eac202671e3df | C=C1C2CC3CC(C2)CC1C3 | C-[C;H0;D3;+0:1](=[C;D1;H2:2])-C(=O)-O-C1(-C)-[CH;D3;+0:3]2-[C:4]-[C:5]-[C:6]-[CH;D3;+0:7]-1-[C:8]-[C:9]-[C:10]-2>>[C;D1;H2:2]=[C;H0;D3;+0:1]1-[CH;D3;+0:3]2-[C:4]-[C:5]-[C:6]-[CH;D3;+0:7]-1-[C:8]-[C:9]-[C:10]-2 | null | [] | null | null | 3 | HOUR | A reaction, a post-treatment, etc. were conducted in the same operation as in Example 16 except that no magnesium sulfate was used, hexane was used as a solvent, and the reaction was conducted at a refluxing temperature for 3 hours. 1.0 g of a crude product was obtained. However, the yield of 2-methyl-2-adamantyl metha... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Vinyl | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | HO- | CCCCCC | null | 3 | C=C(C)C(=O)OC1(C)C2CC3CC(C2)CC1C3>CCCCCC>C=C1C2CC3CC(C2)CC1C3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a2b58a8b0a4645b499a57b5d1f4c1794 | C=C(C)C(=O)OC1(C)C2CC3CC(C2)CC1C3>>C=C1C2CC3CC(C2)CC1C3 | S(=O)(=O)([O-])[O-].[Mg+2].C(C(=C)C)(=O)OC1(C2CC3CC(CC1C3)C2)C>>C=C1C2CC3CC(CC1C3)C2 | C=C(C)C(=O)O[C:2]1([CH3:1])[CH:3]2[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8]2)[CH2:9][CH:10]1[CH2:11]3>>[CH2:1]=[C:2]1[CH:3]2[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8]2)[CH2:9][CH:10]1[CH2:11]3 | C=C(C)C(=O)OC1(C)C2CC3CC(C2)CC1C3 | C=C1C2CC3CC(C2)CC1C3 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | cd12d6a8e0201a5445d4be27996303713f666ace4621fbfa151e3672c774572b | 27cad7c89c5a8beb43e05c14413ac67e94c3817481825e676e038080f8c821e6 | C=C1C2CC3CC(C2)CC1C3 | C-C(=C)-C(=O)-O-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[C:3](-[C:4])-[C:5])-[C:6](-[C:7])-[C:8]>>[C:4]-[C:3](-[C:5])-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[C:6](-[C:7])-[C:8] | null | [] | null | null | 3 | HOUR | A reaction was conducted at a refluxing temperature for 3 hours using no magnesium sulfate but using a Dean-Stark dehydrating apparatus. Toluene was used as a solvent. The other operating conditions were the same as in Example 16, and a reaction, a post-treatment, etc. were conducted. 1.0 g of a crude product was obtai... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Vinyl | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | HO- | C1(=CC=CC=C1)C | null | 3 | C=C(C)C(=O)OC1(C)C2CC3CC(C2)CC1C3>C1(=CC=CC=C1)C>C=C1C2CC3CC(C2)CC1C3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a18b41a08b20496fb73389522c8f22e3 | O=C(O)CC1(CC(=O)O)CCCCC1.[NH4+]>>O=C1CC2(CCCCC2)CC(=O)N1 | C(C)(=O)OC(C)=O.C(C)(=O)[O-].[NH4+].C1(CCCCC1)(CC(=O)O)CC(=O)O>>C1CCC2(CC1)CC(=O)NC(=O)C2 | O[C:2](=[O:1])[CH2:3][C:4]1([CH2:10][C:11](O)=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1.[NH4+:13]>>[O:1]=[C:2]1[CH2:3][C:4]2([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:10][C:11](=[O:12])[NH:13]1 | O=C(O)CC1(CC(=O)O)CCCCC1.[NH4+] | O=C1CC2(CCCCC2)CC(=O)N1 | null | null | null | Acylation | OtherReaction | 56081804e3db793fe8da19ea79241d57b2829aca878df29b3ab8e0b9e8843ee5 | 286fbd2cccb868855ca34a2d629ab8d8113cbdbf5f1fb5f1c2174808f1aa7a3a | O=C1CC2(CCCCC2)CC(=O)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6](-O)=[O;D1;H0:7].[NH4+;D0:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-1 | null | [] | null | null | null | null | reacting a mixture of acetic anhydride/ammonium acetate with 1,1-cyclohexane-diacetic acid to yield 3,3-pentamethylene glutarimide;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Unsubstituted dicarboximide | null | C1CCC2(CC1)CCNCC2 | C1CCC2(CC1)CCNCC2 | HO- | null | null | null | O=C(O)CC1(CC(=O)O)CCCCC1.[NH4+]>>O=C1CC2(CCCCC2)CC(=O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f0be5e581c264314b717384afeda3cb5 | CC#N.COC(=O)C1=C(C(=O)OC)C(Br)CC1>>COC(=O)C1=C(C(=O)OC)C(C#N)CC1 | COC(=O)C1=C(C(CC1)Br)C(=O)OC.C(C)#N>>COC(=O)C1=C(C(CC1)C#N)C(=O)OC | C[C:12]#[N:13].Br[CH:11]1[C:6]([C:7](=[O:8])[O:9][CH3:10])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:15][CH2:14]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([C:7](=[O:8])[O:9][CH3:10])[CH:11]([C:12]#[N:13])[CH2:14][CH2:15]1 | CC#N.COC(=O)C1=C(C(=O)OC)C(Br)CC1 | COC(=O)C1=C(C(=O)OC)C(C#N)CC1 | null | [C-]#N.C(C)[N+](CC)(CC)CC | null | C-C Coupling | OtherReaction | b9727830b5add0049a6799a99d456901615d619c3d3794d9e4e6040d606d8ff9 | c63174dcfcd583644d0faa16ff973ab4b07397cede9ea06d264b491dafe4aa2a | C1=CCCC1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5](-[#8:6])=[O;D1;H0:7])=[C:8]-1-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12].C-[C;H0;D2;+0:13]#[N;D1;H0:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]1=[C:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12])-[CH;D3;+0:1](-[C;H0;D2;+0:13]#[N;D1;H0:14])-[C:2]-[C:3]-1 | 25 | [{"value": 25.0, "product": "COC(=O)C1=C(C(CC1)C#N)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Bromo-cyclopent-1-ene-1,2-dicarboxylic acid dimethyl ester was dissolved in acetonitril under inert conditions. Tetraethylammoniumcyanide (1.1 eq) was added in one portion. The mixture was stirred under inert gas until the reaction was finished (2 h monitored by TLC). The solvent was removed in vacuum and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Nitrile | Nitrile | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | HBr | [C-]#N.C(C)[N+](CC)(CC)CC | null | null | CC#N.COC(=O)C1=C(C(=O)OC)C(Br)CC1>[C-]#N.C(C)[N+](CC)(CC)CC>COC(=O)C1=C(C(=O)OC)C(C#N)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-288b99af453e4009bbf2075cf217e681 | CC(Br)Br.COC(=O)CC(C)=O>>COC(=O)C1(C(C)=O)CC1 | COC(CC(=O)C)=O.C([O-])([O-])=O.[K+].[K+].BrC(C)Br>>COC(=O)C1(CC1)C(C)=O | Br[CH:10](Br)[CH3:9].[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]([CH3:7])=[O:8]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([C:6]([CH3:7])=[O:8])[CH2:9][CH2:10]1 | CC(Br)Br.COC(=O)CC(C)=O | COC(=O)C1(C(C)=O)CC1 | null | null | CC(=O)C.C(C)(=O)OCC | C-C Coupling | OtherReaction | 5009e0f386d6a943363134fef142dab2916acfaa667767ee4ec95372a04438f0 | 8c72ef2f0639f17f3167ada388fb35c02bb00c8c4d1dcba8be13e07686793263 | C1CC1 | Br-[CH;D3;+0:1](-Br)-[CH3;D1;+0:2].[C;D1;H3:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])=[O;D1;H0:10]>>[C;D1;H3:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[C;H0;D4;+0:7]1(-[C:8](-[C;D1;H3:9])=[O;D1;H0:10])-[CH2;D2;+0:1]-[CH2;D2;+0:2]-1 | null | [] | 50 | CELSIUS | 72 | HOUR | 56 g of acetoacetic acid methyl ester 3 is dissolved in 500 ml of acetone, and 276.2 g of potassium carbonate as well as 86 ml of dibromoethane are added while being cooled with ice. It is heated under nitrogen to 50° C. and stirred for 72 hours at this temperature. After cooling, the mixture is diluted with ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Ketone.Ester | Ketone.Ester | null | C1CC1 | C1CC1 | HBr | CC(=O)C.C(C)(=O)OCC | 50 | 72 | CC(Br)Br.COC(=O)CC(C)=O>CC(=O)C.C(C)(=O)OCC>COC(=O)C1(C(C)=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ed8556d158984fafbc05312413177320 | COC(=O)C1(C(C)=O)CC1.OCCO>>COC(=O)C1(C2(C)OCCO2)CC1 | C([O-])(O)=O.[Na+].C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)O)C.COC(=O)C1(CC1)C(C)=O>>COC(=O)C1(CC1)C1(OCCO1)C | [CH3:1][O:2][C:3](=[O:4])[C:5]1([C:6]([CH3:7])=[O:8])[CH2:12][CH2:13]1.O[CH2:9][CH2:10][OH:11]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([C:6]2([CH3:7])[O:8][CH2:9][CH2:10][O:11]2)[CH2:12][CH2:13]1 | COC(=O)C1(C(C)=O)CC1.OCCO | COC(=O)C1(C2(C)OCCO2)CC1 | null | null | C1=CC=CC=C1.O | Heteroatom Alkylation and Arylation | OtherReaction | 2baa95c632045e217509d8ec12cda8674252268fe3f8cb44eb2e5ebe0f27c30f | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | C1COC(C2CC2)O1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1(-[C;H0;D3;+0:9](-[C;D1;H3:10])=[O;H0;D1;+0:11])-[C:12]-[C:13]-1>>[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1(-[C;H0;D4;+0:9]2(-[C;D1;H3:10])-[O;H0;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-2)-[C:12]-[C:13]-1 | null | [] | null | null | null | null | 18.7 g of 4 is dissolved in 500 ml of benzene, 30 ml of ethylene glycol and 1 g of p-toluenesulfonic acid are added and heated under nitrogen in a water separator for 12 hours. After cooling, sodium bicarbonate solution is added, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation, whe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | C1COCO1.C1CC1 | HO- | C1=CC=CC=C1.O | null | null | COC(=O)C1(C(C)=O)CC1.OCCO>C1=CC=CC=C1.O>COC(=O)C1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-defb7654daa34a208c68c11dbb800b7a | COC(=O)C1(C2(C)OCCO2)CC1>>CC1(C2(CO)CC2)OCCO1 | CC(C)C[AlH]CC(C)C.COC(=O)C1(CC1)C1(OCCO1)C.C(C)(C)O.O>>CC1(OCCO1)C1(CC1)CO | CO[C:4]([C:3]1([C:2]2([CH3:1])[O:8][CH2:9][CH2:10][O:11]2)[CH2:6][CH2:7]1)=[O:5]>>[CH3:1][C:2]1([C:3]2([CH2:4][OH:5])[CH2:6][CH2:7]2)[O:8][CH2:9][CH2:10][O:11]1 | COC(=O)C1(C2(C)OCCO2)CC1 | CC1(C2(CO)CC2)OCCO1 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1COC(C2CC2)O1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]1(-[C:4](-[#8:5])-[#8:6])-[C:7]-[C:8]-1>>[#8:5]-[C:4](-[C:3]1(-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:7]-[C:8]-1)-[#8:6] | null | [] | 0 | CELSIUS | null | null | 11.2 g of 5 is dissolved in 150 ml of toluene and cooled under nitrogen to 0° C. 125 ml of DIBAH solution (1.2 M in toluene) is now slowly added in drops and stirred for 2 more hours. Then, 1.25 ml of isopropanol and 25 ml of water are added in drops and stirred overnight. The precipitate is filtered off, the filtrate ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC1.C1COCO1 | Other | C1(=CC=CC=C1)C | 0 | null | COC(=O)C1(C2(C)OCCO2)CC1>C1(=CC=CC=C1)C>CC1(C2(CO)CC2)OCCO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-57f9bc4b3818405e91fe86ee9d699db9 | CC1(C2(CO)CC2)OCCO1>>CC1(C2(C=O)CC2)OCCO1 | CC1(OCCO1)C1(CC1)CO.C(C)(=O)[O-].[Na+].[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>CC1(OCCO1)C1(CC1)C=O | [CH3:1][C:2]1([C:3]2([CH2:4][OH:5])[CH2:6][CH2:7]2)[O:8][CH2:9][CH2:10][O:11]1>>[CH3:1][C:2]1([C:3]2([CH:4]=[O:5])[CH2:6][CH2:7]2)[O:8][CH2:9][CH2:10][O:11]1 | CC1(C2(CO)CC2)OCCO1 | CC1(C2(C=O)CC2)OCCO1 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1COC(C2CC2)O1 | [#8:1]-[C:2](-[C:3]1(-[CH2;D2;+0:4]-[OH;D1;+0:5])-[C:6]-[C:7]-1)-[#8:8]>>[#8:1]-[C:2](-[C:3]1(-[CH;D2;+0:4]=[O;H0;D1;+0:5])-[C:6]-[C:7]-1)-[#8:8] | 79 | [{"value": 79.0, "product": "CC1(OCCO1)C1(CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 10 g of 6 is dissolved in 500 ml of dichloromethane, and 3.7 g of sodium acetate and 19.3 g of pyridinium chlorochromate are added at room temperature under nitrogen. After 3 hours at room temperature, it is filtered on silica gel, concentrated by evaporation, diluted with diethyl ether, filtered again, and the solvent... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CC1.C1COCO1 | null | ClCCl | null | 3 | CC1(C2(CO)CC2)OCCO1>ClCCl>CC1(C2(C=O)CC2)OCCO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-97f445886d124fe785ad845c9c6fd3fd | CC1(C2(C=O)CC2)OCCO1>>C=CC1(C2(C)OCCO2)CC1 | C(CCC)[Li].CC1(OCCO1)C1(CC1)C=O>>C(=C)C1(CC1)C1(OCCO1)C | O=[CH:2][C:3]1([C:4]2([CH3:5])[O:6][CH2:7][CH2:8][O:9]2)[CH2:10][CH2:11]1>>[CH2:1]=[CH:2][C:3]1([C:4]2([CH3:5])[O:6][CH2:7][CH2:8][O:9]2)[CH2:10][CH2:11]1 | CC1(C2(C=O)CC2)OCCO1 | C=CC1(C2(C)OCCO2)CC1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)OCC | Functional Group Interconversion | OtherReaction | dd6fb167b4e71f3ea190d18ad4e87d18c641d879b83b47beb9dc06bc791584b1 | 6b3ec9b506a5bb4882685e77a1e07fcb518f891061dfbc2d36767289330c841e | C1COC(C2CC2)O1 | O=[CH;D2;+0:1]-[C:2]1(-[C:3](-[#8:4])-[#8:5])-[C:6]-[C:7]-1>>[#8:4]-[C:3](-[C:2]1(-[CH;D2;+0:1]=[C;D1;H2:8])-[C:6]-[C:7]-1)-[#8:5] | null | [] | null | null | 1 | HOUR | 44.6 g of methyltriphenylphosphonium bromide in 700 ml of diethyl ether is introduced, and 50 ml of n-butyllithium solution (2.5 M in hexane) is added in drops at 0° C. under nitrogen. It is stirred for 1 more hour at room temperature and then 9.5 g of 7 in 10 ml of diethyl ether is added. After 1 hour, the reaction so... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Vinyl | null | null | C1COCO1.C1CC1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)OCC | null | 1 | CC1(C2(C=O)CC2)OCCO1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)OCC>C=CC1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5f9a49c677524ef5847fd01a3d22ff13 | C=CC1(C2(C)OCCO2)CC1.OO>>CC1(C2(CCO)CC2)OCCO1 | C(=C)C1(CC1)C1(OCCO1)C.[OH-].[Na+].OO.S(=S)(=O)([O-])[O-].[Na+].[Na+].B.O1CCCC1>>CC1(OCCO1)C1(CC1)CCO | [CH3:1][C:2]1([C:3]2([CH:4]=[CH2:5])[CH2:7][CH2:8]2)[O:9][CH2:10][CH2:11][O:12]1.O[OH:6]>>[CH3:1][C:2]1([C:3]2([CH2:4][CH2:5][OH:6])[CH2:7][CH2:8]2)[O:9][CH2:10][CH2:11][O:12]1 | C=CC1(C2(C)OCCO2)CC1.OO | CC1(C2(CCO)CC2)OCCO1 | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 6aaa6688cc4965019d9400c93c20e1d817a445418a6601722f66df7d420427e9 | 4ceb30033bcfd57c382fe05e353b68e7f657859dbacaaa785451a244b2657476 | C1COC(C2CC2)O1 | O-[OH;D1;+0:1].[#8:2]-[C:3](-[C:4]1(-[CH;D2;+0:5]=[CH2;D1;+0:6])-[C:7]-[C:8]-1)-[#8:9]>>[#8:2]-[C:3](-[C:4]1(-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[OH;D1;+0:1])-[C:7]-[C:8]-1)-[#8:9] | null | [] | null | null | null | null | 5.4 g of 8 is dissolved in 200 ml of tetrahydrofuran (THF), and 14 ml of borane-THF solution (1.0 M in THF) is added in drops at 0° C. under nitrogen. The reaction mixture is then allowed to reach room temperature, and it is stirred for 2 more hours. After cooling was again performed at 0° C., 17 ml of water, 17 ml of ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Vinyl | Primary alcohol | null | null | C1CC1.C1COCO1 | Other | O1CCCC1.O | null | null | C=CC1(C2(C)OCCO2)CC1.OO>O1CCCC1.O>CC1(C2(CCO)CC2)OCCO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00d9a39c35f54c10bf5709b7fb250eb9 | CC1(C2(CCO)CC2)OCCO1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OCCC2(C3(C)OCCO3)CC2)cc1 | CC1(OCCO1)C1(CC1)CCO.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C([O-])(O)=O.[Na+]>>CC1(OCCO1)C1(CC1)CCOS(=O)(=O)C1=CC=C(C=C1)C | [OH:9][CH2:10][CH2:11][C:12]1([C:13]2([CH3:14])[O:15][CH2:16][CH2:17][O:18]2)[CH2:19][CH2:20]1.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:22][cH:21]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][C:12]2([C:13]3([CH3:14])[O:15][CH2:16][CH2:17][O:18]3)[CH2:19][CH2:20]2)[cH:21]... | CC1(C2(CCO)CC2)OCCO1.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OCCC2(C3(C)OCCO3)CC2)cc1 | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(OCCC1(C2OCCO2)CC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | 1 | HOUR | 470 mg of 9 is dissolved in 10 ml of pyridine, and p-toluenesulfonyl chloride is added at 0° C. under nitrogen. It is stirred for 1 hour at 0° C., and then sodium bicarbonate solution is added. It is extracted with ethyl acetate, washed with dilute hydrochloric acid and then with sodium bicarbonate solution, dried on s... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.C1COCO1.C1CC1 | HCl | N1=CC=CC=C1 | 0 | 1 | CC1(C2(CCO)CC2)OCCO1.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1>Cc1ccc(S(=O)(=O)OCCC2(C3(C)OCCO3)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1ecf1a0e096f46bc8ab8d467c091a4ea | Cc1ccc(S(=O)(=O)OCCC2(C3(C)OCCO3)CC2)cc1.Sc1ccccc1>>CC1(C2(CCSc3ccccc3)CC2)OCCO1 | C1(=CC=CC=C1)S.CC1(OCCO1)C1(CC1)CCOS(=O)(=O)C1=CC=C(C=C1)C>>CC1(OCCO1)C1(CC1)CCSC1=CC=CC=C1 | Cc1ccc(S(=O)(=O)O[CH2:5][CH2:4][C:3]2([C:2]3([CH3:1])[O:15][CH2:16][CH2:17][O:18]3)[CH2:13][CH2:14]2)cc1.[SH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C:2]1([C:3]2([CH2:4][CH2:5][S:6][c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[CH2:13][CH2:14]2)[O:15][CH2:16][CH2:17][O:18]1 | Cc1ccc(S(=O)(=O)OCCC2(C3(C)OCCO3)CC2)cc1.Sc1ccccc1 | CC1(C2(CCSc3ccccc3)CC2)OCCO1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | fa9f9600581ef05dca04b54e63c21080ab3037c0f706082a272f2da0c08c4f32 | 8d10c46c4c89029273335615fb077055d8239c352e37ee1740069c99de11581b | c1ccc(SCCC2(C3OCCO3)CC2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3]):c:c:1.[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | 590 mg of 10 is dissolved in 2 ml of dimethylformamide (DMF) and added under nitrogen to a mixture of 300 mg of potassium-t-butylate and 0.27 ml of thiophenol in 5 ml of DMF. It is stirred for 1 hour at room temperature and then quenched with sodium chloride solution. It is extracted with ethyl acetate, washed with sod... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic thiol | Monosulfide | c1ccccc1 | null | c1ccccc1.C1CC1.C1COCO1 | TsOH.HO- | CN(C=O)C | null | 1 | Cc1ccc(S(=O)(=O)OCCC2(C3(C)OCCO3)CC2)cc1.Sc1ccccc1>CN(C=O)C>CC1(C2(CCSc3ccccc3)CC2)OCCO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbe3e6451b744424b549660e3fb4baea | CCI.COC(=O)CC(C)=O>>CCCC(=O)CC(=O)OC | [H-].[Na+].COC(CC(=O)C)=O.Cl.ICC.C(CCC)[Li]>>COC(CC(CCC)=O)=O | I[CH2:2][CH3:1].[CH3:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH3:10]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH3:10] | CCI.COC(=O)CC(C)=O | CCCC(=O)CC(=O)OC | null | null | C(C)(=O)OCC.C1CCOC1 | C-C Coupling | OtherReaction | e8b75e5efb691ecf3c9116420e15918cdd0fda7b899536fb179ed39cbdad1bc2 | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | null | I-[CH2;D2;+0:1]-[C;D1;H3:2].[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7](-[CH3;D1;+0:8])=[O;D1;H0:9]>>[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7](=[O;D1;H0:9])-[CH2;D2;+0:8]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 10 | MINUTE | 44.4 g of sodium hydride suspension (60% in paraffin oil) is introduced into 1500 ml of THF, and 107.5 ml of acetoacetic acid methyl ester 3 is added under nitrogen at 0° C. After 10 minutes, 440 ml of n-butyllithium solution (2.5 M in hexane) is then added in drops, and it is stirred for another 30 minutes at 0C. Now,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | null | null | null | HI | C(C)(=O)OCC.C1CCOC1 | null | 0.166667 | CCI.COC(=O)CC(C)=O>C(C)(=O)OCC.C1CCOC1>CCCC(=O)CC(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-471da5d51b6b4cea9d594e1b3d56f24b | CC1(C2(C=O)CC2)OCCO1.COC(=O)CP(=O)(OC)OC>>COC(=O)/C=C/C1(C2(C)OCCO2)CC1 | COC(CP(=O)(OC)OC)=O.[H-].[Na+].CC1(OCCO1)C1(CC1)C=O>>COC(\C=C\C1(CC1)C1(OCCO1)C)=O | O=[CH:6][C:7]1([C:8]2([CH3:9])[O:10][CH2:11][CH2:12][O:13]2)[CH2:14][CH2:15]1.COP(=O)(OC)[CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:6]/[C:7]1([C:8]2([CH3:9])[O:10][CH2:11][CH2:12][O:13]2)[CH2:14][CH2:15]1 | CC1(C2(C=O)CC2)OCCO1.COC(=O)CP(=O)(OC)OC | COC(=O)/C=C/C1(C2(C)OCCO2)CC1 | null | null | C1CCOC1 | C-C Coupling | Wittig with Phosphonium | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | C1COC(C2CC2)O1 | C-O-P(=O)(-O-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].O=[CH;D2;+0:6]-[C:7]1(-[C:8](-[#8:9])-[#8:10])-[C:11]-[C:12]-1>>[#8:9]-[C:8](-[C:7]1(/[CH;D2;+0:6]=[CH;D2;+0:1]/[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C:11]-[C:12]-1)-[#8:10] | null | [] | 0 | CELSIUS | 2 | HOUR | 3 g of sodium hydride suspension (60% in paraffin oil) is introduced into 750 ml of THF, cooled under nitrogen to 0° C., and 10.9 g of dimethylphosphonoacetic acid methyl ester is added. Then, 7.5 g of aldehyde 7 is added in drops to 15 ml of THF, and it is stirred at room temperature for 2 hours. It is now quenched ca... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | C1COCO1.C1CC1 | HO- | C1CCOC1 | 0 | 2 | CC1(C2(C=O)CC2)OCCO1.COC(=O)CP(=O)(OC)OC>C1CCOC1>COC(=O)/C=C/C1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5acf844c5c24b999fc9ae28f72b4c88 | CC1(C2(C=O)CC2)OCCO1.COP(=O)(CCC=O)OC>>CC(=O)/C=C/C1(C2(C)OCCO2)CC1 | [Cl-].[Li+].[Cl-].[Na+].COP(OC)(=O)CCC=O.C(C)(C)N(CC)C(C)C.CC1(OCCO1)C1(CC1)C=O>>CC1(OCCO1)C1(CC1)/C=C/C(C)=O | O=[CH:5][C:6]1([C:7]2([CH3:8])[O:9][CH2:10][CH2:11][O:12]2)[CH2:13][CH2:14]1.COP(=O)(OC)[CH2:1][CH2:4][CH:2]=[O:3]>>[CH3:1][C:2](=[O:3])/[CH:4]=[CH:5]/[C:6]1([C:7]2([CH3:8])[O:9][CH2:10][CH2:11][O:12]2)[CH2:13][CH2:14]1 | CC1(C2(C=O)CC2)OCCO1.COP(=O)(CCC=O)OC | CC(=O)/C=C/C1(C2(C)OCCO2)CC1 | null | null | C(C)#N | C-C Coupling | OtherReaction | 21db8d37c05aca84b4f073906818d205da271deee49cf0ba6c7250be992af972 | b0501e2687bea7d8a21f333ccfaded99e607958f8cf0f177a5f87c801870e4ba | C1COC(C2CC2)O1 | C-O-P(=O)(-O-C)-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH;D2;+0:3]=[O;D1;H0:4].O=[CH;D2;+0:5]-[C:6]1(-[C:7](-[#8:8])-[#8:9])-[C:10]-[C:11]-1>>[#8:8]-[C:7](-[C:6]1(/[CH;D2;+0:5]=[CH;D2;+0:2]/[C;H0;D3;+0:3](-[CH3;D1;+0:1])=[O;D1;H0:4])-[C:10]-[C:11]-1)-[#8:9] | null | [] | null | null | 18 | HOUR | 13.8 g of lithium chloride (anhydrous) is introduced into 120 ml of acetonitrile under nitrogen, and 49.8 ml of oxopropylphosphonic acid dimethyl ester, 51.3 ml of diisopropylethylamine and 5.4 g of aldehyde 7 are added in succession. It is stirred for 18 hours at room temperature, and then sodium chloride solution is ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Ketone | null | null | C1COCO1.C1CC1 | HO- | C(C)#N | null | 18 | CC1(C2(C=O)CC2)OCCO1.COP(=O)(CCC=O)OC>C(C)#N>CC(=O)/C=C/C1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-94c948cc57194278aef42c5ab3b35ba8 | CC(=O)/C=C/C1(C2(C)OCCO2)CC1>>CC(=O)CCC1(C2(C)OCCO2)CC1 | CC1(OCCO1)C1(CC1)/C=C/C(C)=O.[H][H]>>CC1(OCCO1)C1(CC1)CCC(C)=O | [CH3:1][C:2](=[O:3])/[CH:4]=[CH:5]/[C:6]1([C:7]2([CH3:8])[O:9][CH2:10][CH2:11][O:12]2)[CH2:13][CH2:14]1>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][C:6]1([C:7]2([CH3:8])[O:9][CH2:10][CH2:11][O:12]2)[CH2:13][CH2:14]1 | CC(=O)/C=C/C1(C2(C)OCCO2)CC1 | CC(=O)CCC1(C2(C)OCCO2)CC1 | null | [Pt](=O)=O | C1CCOC1 | Reduction | Hydrogenation (double to single) | 6556ac5f7a00160b061cac263043ece7ea2394a4006031c4a0b899c0ea4ccfef | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | C1COC(C2CC2)O1 | [#8:1]-[C:2](-[C:3]1(/[CH;D2;+0:4]=[CH;D2;+0:5]/[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9]-[C:10]-1)-[#8:11]>>[#8:1]-[C:2](-[C:3]1(-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9]-[C:10]-1)-[#8:11] | null | [] | null | null | null | null | 1.23 g of 153 is dissolved in THF, and 200 mg of platinum(IV) oxide is added in an argon stream. Using a hydrogenating apparatus, it is hydrogenated until no more hydrogen is consumed, flushed with nitrogen, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | null | null | C1COCO1.C1CC1 | null | [Pt](=O)=O.C1CCOC1 | null | null | CC(=O)/C=C/C1(C2(C)OCCO2)CC1>[Pt](=O)=O.C1CCOC1>CC(=O)CCC1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f2172af70fa4b9d89d9973bf5fff44b | C=CC1(C2(C)OCCO2)CC1>>CCC1(C2(C)OCCO2)CC1 | C(=C)C1(CC1)C1(OCCO1)C.[H][H]>>C(C)C1(CC1)C1(OCCO1)C | [CH2:1]=[CH:2][C:3]1([C:4]2([CH3:5])[O:6][CH2:7][CH2:8][O:9]2)[CH2:10][CH2:11]1>>[CH3:1][CH2:2][C:3]1([C:4]2([CH3:5])[O:6][CH2:7][CH2:8][O:9]2)[CH2:10][CH2:11]1 | C=CC1(C2(C)OCCO2)CC1 | CCC1(C2(C)OCCO2)CC1 | null | [Pt](=O)=O | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | C1COC(C2CC2)O1 | [#8:1]-[C:2](-[C:3]1(-[CH;D2;+0:4]=[CH2;D1;+0:5])-[C:6]-[C:7]-1)-[#8:8]>>[#8:1]-[C:2](-[C:3]1(-[CH2;D2;+0:4]-[CH3;D1;+0:5])-[C:6]-[C:7]-1)-[#8:8] | 78.6 | [{"value": 78.6, "product": "C(C)C1(CC1)C1(OCCO1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 500 mg of olefin 8 is dissolved in 15 ml of ethyl acetate, 150 mg of platinum(IV) oxide is added and hydrogenated in a hydrogenating apparatus until no more hydrogen is taken up. After filtration, it is concentrated by evaporation, whereby 398 mg of title compound 195 is obtained as a colorless oil, which is immediatel... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | C1COCO1.C1CC1 | null | [Pt](=O)=O.C(C)(=O)OCC | null | null | C=CC1(C2(C)OCCO2)CC1>[Pt](=O)=O.C(C)(=O)OCC>CCC1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3dff8306754042b4ab9952d4825cd9e0 | CC1(C2(C=O)CC2)OCCO1.CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCC=CC1(C2(C)OCCO2)CC1 | CC1(OCCO1)C1(CC1)C=O.[Br-].C(CC)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)[Li]>>C(=CCC)C1(CC1)C1(OCCO1)C | O=[CH:4][C:5]1([C:6]2([CH3:7])[O:8][CH2:9][CH2:10][O:11]2)[CH2:12][CH2:13]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:3][CH2:2][CH3:1])cc1>>[CH3:1][CH2:2][CH:3]=[CH:4][C:5]1([C:6]2([CH3:7])[O:8][CH2:9][CH2:10][O:11]2)[CH2:12][CH2:13]1 | CC1(C2(C=O)CC2)OCCO1.CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CCC=CC1(C2(C)OCCO2)CC1 | null | null | C(C)OCC | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C1COC(C2CC2)O1 | O=[CH;D2;+0:1]-[C:2]1(-[C:3](-[#8:4])-[#8:5])-[C:6]-[C:7]-1.[C;D1;H3:8]-[C:9]-[CH2;D2;+0:10]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#8:4]-[C:3](-[C:2]1(-[CH;D2;+0:1]=[CH;D2;+0:10]-[C:9]-[C;D1;H3:8])-[C:6]-[C:7]-1)-[#8:5] | null | [] | null | null | 1 | HOUR | 7.2 g of propyltriphenylphosphonium bromide is dissolved in 100 ml of diethyl ether, and 7.5 ml of n-butyllithium solution (2.5 M in hexane) is added in drops under nitrogen at room temperature. It is stirred for 1 hour, and then 2.34 g of aldehyde 7 is added to 10 ml of diethyl ether. It is stirred for 1 more hour, qu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1COCO1.C1CC1 | HO- | C(C)OCC | null | 1 | CC1(C2(C=O)CC2)OCCO1.CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C(C)OCC>CCC=CC1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c74e7f546924d35934b1d90c6516f3d | CC1(C2(C=O)CC2)OCCO1.CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCC=CC1(C2(C)OCCO2)CC1 | [Br-].C(CCCC)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1(OCCO1)C1(CC1)C=O>>C(=CCCCC)C1(CC1)C1(OCCO1)C | O=[CH:6][C:7]1([C:8]2([CH3:9])[O:10][CH2:11][CH2:12][O:13]2)[CH2:14][CH2:15]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH:6][C:7]1([C:8]2([CH3:9])[O:10][CH2:11][CH2:12][O:13]2)[CH2:14][CH2:15]1 | CC1(C2(C=O)CC2)OCCO1.CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCC=CC1(C2(C)OCCO2)CC1 | null | null | null | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C1COC(C2CC2)O1 | O=[CH;D2;+0:1]-[C:2]1(-[C:3](-[#8:4])-[#8:5])-[C:6]-[C:7]-1.[C:8]-[C:9]-[CH2;D2;+0:10]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#8:4]-[C:3](-[C:2]1(-[CH;D2;+0:1]=[CH;D2;+0:10]-[C:9]-[C:8])-[C:6]-[C:7]-1)-[#8:5] | null | [] | null | null | null | null | 2.07 g of pentyltriphenylphosphonium bromide and 600 mg of aldehyde 7 are reacted analogously to 193., and 567 g of title substance 200 is obtained as a colorless oil (8:1 E,Z-mixture that cannot be separated).
Conditions: See reaction.notes.procedure_details.
Workup: , and 567 g of title substance 200 is obtained as a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1COCO1.C1CC1 | HO- | null | null | null | CC1(C2(C=O)CC2)OCCO1.CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCC=CC1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3b3811c49ec430b9bcb1f0aa72e085a | CC1(C2(C=O)CC2)OCCO1.CCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCC=CC1(C2(C)OCCO2)CC1 | [Br-].C(CCCCC)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1(OCCO1)C1(CC1)C=O>>C(=CCCCCC)C1(CC1)C1(OCCO1)C | O=[CH:7][C:8]1([C:9]2([CH3:10])[O:11][CH2:12][CH2:13][O:14]2)[CH2:15][CH2:16]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][C:8]1([C:9]2([CH3:10])[O:11][CH2:12][CH2:13][O:14]2)[CH2:15][CH2:16]1 | CC1(C2(C=O)CC2)OCCO1.CCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCC=CC1(C2(C)OCCO2)CC1 | null | null | null | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C1COC(C2CC2)O1 | O=[CH;D2;+0:1]-[C:2]1(-[C:3](-[#8:4])-[#8:5])-[C:6]-[C:7]-1.[C:8]-[C:9]-[CH2;D2;+0:10]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#8:4]-[C:3](-[C:2]1(-[CH;D2;+0:1]=[CH;D2;+0:10]-[C:9]-[C:8])-[C:6]-[C:7]-1)-[#8:5] | null | [] | null | null | null | null | 1.93 g of hexyltriphenylphosphonium bromide and 900 mg of aldehyde 7 are reacted analogously to 193., and 879 mg of title substance 203 is obtained as a colorless oil (1:3 E,Z mixture that cannot be separated).
Conditions: See reaction.notes.procedure_details.
Workup: , and 879 mg of title substance 203 is obtained as ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1COCO1.C1CC1 | HO- | null | null | null | CC1(C2(C=O)CC2)OCCO1.CCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCC=CC1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72ef0d959b81425ab540df2aa60f8e0a | CC1(C2(C=O)CC2)OCCO1.CCCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCC/C=C\C1(C2(C)OCCO2)CC1 | [Br-].C(CCCCCC)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1(OCCO1)C1(CC1)C=O>>CC1(OCCO1)C1(CC1)\C=C/CCCCCC | O=[CH:8][C:9]1([C:10]2([CH3:11])[O:12][CH2:13][CH2:14][O:15]2)[CH2:16][CH2:17]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[C:9]1([C:10]2([CH3:11])[O:12][CH2:13][CH2:14][O:15]2)[CH2:16][CH2:17]1 | CC1(C2(C=O)CC2)OCCO1.CCCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCC/C=C\C1(C2(C)OCCO2)CC1 | null | null | null | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C1COC(C2CC2)O1 | O=[CH;D2;+0:1]-[C:2]1(-[C:3](-[#8:4])-[#8:5])-[C:6]-[C:7]-1.[C:8]-[C:9]-[CH2;D2;+0:10]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#8:4]-[C:3](-[C:2]1(/[CH;D2;+0:1]=[CH;D2;+0:10]\[C:9]-[C:8])-[C:6]-[C:7]-1)-[#8:5] | null | [] | null | null | null | null | 4.87 g of heptyltriphenylphosphonium bromide and 1.25 g of aldehyde 7 are reacted analogously to 193., and 978 mg of title substance 206 is obtained as a colorless oil (only Z-isomer).
Conditions: See reaction.notes.procedure_details.
Workup: , and 978 mg of title substance 206 is obtained as a colorless oil (only Z-is... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1COCO1.C1CC1 | HO- | null | null | null | CC1(C2(C=O)CC2)OCCO1.CCCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCC/C=C\C1(C2(C)OCCO2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-08e9eb19e15d4e6fa1eb511e4a67f7f7 | CCOC(=O)c1cc2cc(O)ccc2[nH]1.CN(C)C(=O)CCl>>CCOC(=O)c1cc2cc(OCC(=O)N(C)C)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)O.ClCC(=O)N(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(N(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[cH:18][cH:19][c:20]2[nH:21]1.Cl[CH2:12][C:13](=[O:14])[N:15]([CH3:16])[CH3:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[N:15]([CH3:16])[CH3:17])[cH:18][cH:19][c:20]2[nH:21]1 | CCOC(=O)c1cc2cc(O)ccc2[nH]1.CN(C)C(=O)CCl | CCOC(=O)c1cc2cc(OCC(=O)N(C)C)ccc2[nH]1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2[nH]ccc2c1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C;D1;H3:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:5]-[#7:4](-[C;D1;H3:6])-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 48.2 | [{"value": 48.2, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(N(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (2 g, 10 mmol), 2-chloro-N,N-dimethylacetamide (1.33 g, 11 mmol) and cesium carbonate (9.8 g, 30 mmol)) in dimethylformamide (20 mL) was stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate (150 mL), washed with water (5×50 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 16 | CCOC(=O)c1cc2cc(O)ccc2[nH]1.CN(C)C(=O)CCl>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)c1cc2cc(OCC(=O)N(C)C)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5c9fd879bc148bb9d2bae474ded4855 | CCOC(=O)c1cc2cc(OCC(=O)N(C)C)ccc2[nH]1>>CN(C)CCOc1ccc2[nH]c(CO)cc2c1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(N(C)C)=O>>CN(CCOC=1C=C2C=C(NC2=CC1)CO)C | CCO[C:13]([c:12]1[nH:11][c:10]2[cH:9][cH:8][c:7]([O:6][CH2:5][C:4](=O)[N:2]([CH3:1])[CH3:3])[cH:17][c:16]2[cH:15]1)=[O:14]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]2[nH:11][c:12]([CH2:13][OH:14])[cH:15][c:16]2[cH:17]1 | CCOC(=O)c1cc2cc(OCC(=O)N(C)C)ccc2[nH]1 | CN(C)CCOc1ccc2[nH]c(CO)cc2c1 | null | null | O1CCCC1 | Reduction | OtherReaction | c69e55c870fca7a48716cf1a13d3b1c66b1429a862fb2c663e47b4c648179c46 | a65143cb02ef97811e30a8153880ab0c649a356c31e2df2bd3a78b2a9b48cbfc | c1ccc2[nH]ccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].O=[C;H0;D3;+0:7](-[C:8]-[#8:9])-[#7:10](-[C;D1;H3:11])-[C;D1;H3:12]>>[#8:9]-[C:8]-[CH2;D2;+0:7]-[#7:10](-[C;D1;H3:11])-[C;D1;H3:12].[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 54 | [{"value": 54.0, "product": "CN(CCOC=1C=C2C=C(NC2=CC1)CO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.4, "product": "CN(CCOC=1C=C2C=C(NC2=CC1)CO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Lithium aluminum hydride (1.7 g, 45 mmol) was added to 5-dimethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl ester (1.4 g, 4.8 mmol) in tetrahydrofuran (80 mL). The mixture was stirred at room temperature for 4 hours and cooled to 0° C. It was then quenched with water (1.7 mL), 15% sodium hydroxide (1.7 mL) and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide | Primary alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | O1CCCC1 | null | 4 | CCOC(=O)c1cc2cc(OCC(=O)N(C)C)ccc2[nH]1>O1CCCC1>CN(C)CCOc1ccc2[nH]c(CO)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d2d8bd033714cbd9975cd8aff53f74d | C1CCNC1.O=C(Br)CBr>>O=C(CBr)N1CCCC1 | N1CCCC1.BrCC(=O)Br.C(C)N(CC)CC>>BrCC(=O)N1CCCC1 | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1.Br[C:2](=[O:1])[CH2:3][Br:4]>>[O:1]=[C:2]([CH2:3][Br:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1 | C1CCNC1.O=C(Br)CBr | O=C(CBr)N1CCCC1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 5ce41b3db1ff79b8dd0325761a92ce74d9b898070d3b61ae6f52ef2fb0fe31ed | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | C1CCNC1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | 67.3 | [{"value": 67.3, "product": "BrCC(=O)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of pyrrolidine (1.7 g, 24 mmol), bromoacetyl bromide (4.6 g, 24 mmol) and triethylamine (2.02 g, 20 mmol) in dichloromethane (40 mL) was stirred at room temperature for 4 hours. The precipitate was filtered off and the residue was concentrated to give 3.1 g of 2-bromo-1-pyrrolidin-1-yl-ethanone as a light bro... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | HBr | ClCCl | null | 4 | C1CCNC1.O=C(Br)CBr>ClCCl>O=C(CBr)N1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bd3f5973d8154800a333fcc7c94b4117 | CCOC(=O)c1cc2cc(O)ccc2[nH]1.O=C(CBr)N1CCCC1>>CCOC(=O)c1cc2cc(OCC(=O)N3CCCC3)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)O.BrCC(=O)N1CCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(N1CCCC1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[cH:20][cH:21][c:22]2[nH:23]1.Br[CH2:12][C:13](=[O:14])[N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[N:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20][cH:21][c:22... | CCOC(=O)c1cc2cc(O)ccc2[nH]1.O=C(CBr)N1CCCC1 | CCOC(=O)c1cc2cc(OCC(=O)N3CCCC3)ccc2[nH]1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(COc1ccc2[nH]ccc2c1)N1CCCC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[C:6] | 25.3 | [{"value": 25.0, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(N1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.3, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(N1CCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (2 g, 10 mmol), 2-bromo-1-pyrrolidin-1-yl-ethanone (3 g, 20 mmol) and cesium carbonate (19.5 g, 60 mmol) in dimethylformamide (16 mL) was stirred at room temperature for 24 hours. The reaction was diluted with ethyl acetate (150 mL), washed with water (5×50... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 24 | CCOC(=O)c1cc2cc(O)ccc2[nH]1.O=C(CBr)N1CCCC1>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)c1cc2cc(OCC(=O)N3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f06ef23162cf40829f6f7b12ee23801d | CC(C)(C)OC(=O)CBr.CCOC(=O)c1cc2cc(O)ccc2[nH]1>>CCOC(=O)c1cc2cc(OCC(=O)OC(C)(C)C)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)O.BrCC(=O)OC(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)OC(C)(C)C | Br[CH2:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[cH:20][cH:21][c:22]2[nH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21][c:22... | CC(C)(C)OC(=O)CBr.CCOC(=O)c1cc2cc(O)ccc2[nH]1 | CCOC(=O)c1cc2cc(OCC(=O)OC(C)(C)C)ccc2[nH]1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 63 | [{"value": 63.0, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (2 g, 10 mmol), tert-butyl bromoacetate (2.35 g, 12 mmol) and cesium carbonate (10.5 g, 30 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate (150 mL), washed with water (5×50 mL) and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccc2[nH]ccc2c1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 16 | CC(C)(C)OC(=O)CBr.CCOC(=O)c1cc2cc(O)ccc2[nH]1>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)c1cc2cc(OCC(=O)OC(C)(C)C)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1cd0dafad4d04a1f958e81fb95affc08 | CCOC(=O)c1cc2cc(OCC(=O)OC(C)(C)C)ccc2[nH]1>>CCOC(=O)c1cc2cc(OCC(=O)O)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)O | CC(C)(C)[O:15][C:13]([CH2:12][O:11][c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:19][c:18]2[cH:17][cH:16]1)=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[OH:15])[cH:16][cH:17][c:18]2[nH:19]1 | CCOC(=O)c1cc2cc(OCC(=O)OC(C)(C)C)ccc2[nH]1 | CCOC(=O)c1cc2cc(OCC(=O)O)ccc2[nH]1 | null | null | ClCCl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccc2[nH]ccc2c1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 101.3 | [{"value": 97.0, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.3, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 5-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester (2 g, 6 mmol) and trifluoroacetic acid (8 mL) in dichloromethane (8 mL) was stirred at room temperature for 2 hours. The reaction was concentrated to give 1.6 g (97%) of 5-carboxymethoxy-1H-indole-2-carboxylic acid ethyl ester as a light ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1 | Other | ClCCl | null | 2 | CCOC(=O)c1cc2cc(OCC(=O)OC(C)(C)C)ccc2[nH]1>ClCCl>CCOC(=O)c1cc2cc(OCC(=O)O)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8bdb870daaba4cffb7d85aa8ea85fe18 | C1COCCN1.CCOC(=O)c1cc2cc(OCC(=O)O)ccc2[nH]1>>CCOC(=O)c1cc2cc(OCC(=O)N3CCOCC3)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)O.N1CCOCC1>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)N1CCOCC1 | [NH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1.O[C:13]([CH2:12][O:11][c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:24][c:23]2[cH:22][cH:21]1)=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[cH:21][... | C1COCCN1.CCOC(=O)c1cc2cc(OCC(=O)O)ccc2[nH]1 | CCOC(=O)c1cc2cc(OCC(=O)N3CCOCC3)ccc2[nH]1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(COc1ccc2[nH]ccc2c1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | 85 | [{"value": 85.0, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 5-carboxymethoxy-1H-indole-2-carboxylic acid ethyl ester (1.5 g, 5.7 mmol) and 1-1′-carbonyldiimidazole (1.11 g, 6.85 mmol) in dimethylformamide (15 mL) was stirred at room temperature for 30 mins. To the mixture was then added morpholine (1 mL) and the stirring was continued for overnight. The reaction wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccc2[nH]ccc2c1.C1COCC[NH]1 | HO- | CN(C=O)C | null | 0.5 | C1COCCN1.CCOC(=O)c1cc2cc(OCC(=O)O)ccc2[nH]1>CN(C=O)C>CCOC(=O)c1cc2cc(OCC(=O)N3CCOCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e1c4064a4ed436997c164f1d796bf87 | CCOC(=O)c1cc2cc(OCC(=O)N3CCOCC3)ccc2[nH]1>>OCc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(=O)N1CCOCC1>>N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)CO | CCO[C:2](=[O:1])[c:3]1[cH:4][c:5]2[cH:6][c:7]([O:8][CH2:9][C:10](=O)[N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[cH:17][cH:18][c:19]2[nH:20]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([O:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[cH:17][cH:18][c:19]2[nH:20]1 | CCOC(=O)c1cc2cc(OCC(=O)N3CCOCC3)ccc2[nH]1 | OCc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | null | null | O1CCCC1 | Reduction | OtherReaction | c69e55c870fca7a48716cf1a13d3b1c66b1429a862fb2c663e47b4c648179c46 | a65143cb02ef97811e30a8153880ab0c649a356c31e2df2bd3a78b2a9b48cbfc | c1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].O=[C;H0;D3;+0:7](-[C:8]-[#8:9])-[#7:10](-[C:11])-[C:12]>>[#8:9]-[C:8]-[CH2;D2;+0:7]-[#7:10](-[C:11])-[C:12].[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 105.5 | [{"value": 105.5, "product": "N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Lithium aluminum hydride (0.46 g, 12 mmol) was added 5-(2-morpholin-4-yl-2-oxo-ethoxy)-1H-indole-2-carboxylic acid ethyl ester (0.8 g, 2.4 mmol) in tetrahydrofuran (50 mL). The mixture was stirred at room temperature for 16 hours and cooled to 0° C. It was then quenched with water (4.6 mL), 15% sodium hydroxide (4.6 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide | Primary alcohol | null | null | c1ccc2[nH]ccc2c1.C1COCC[NH]1 | Other | O1CCCC1 | null | 16 | CCOC(=O)c1cc2cc(OCC(=O)N3CCOCC3)ccc2[nH]1>O1CCCC1>OCc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d303012ec1434d6ba766c694c2310c35 | OCc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>>O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)CO>>N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=O | [OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([O:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[cH:17][cH:18][c:19]2[nH:20]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([O:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[cH:17][cH:18][c:19]2[nH:20]1 | OCc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | null | [O-2].[Mn+4].[O-2] | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 25.9 | [{"value": 25.9, "product": "N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Manganese (IV) oxide (3.2 g, 36 mmol) was added to [5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-yl]-methanol (0.7 g) in dichloromethane (150 mL). The mixture was stirred at room temperature for 16 hours. The precipitate was filtered off and the filtrate was concentrated. The residue was recrystallized from ethyl acetate and... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2[nH]ccc2c1.C1COCC[NH]1 | null | [O-2].[Mn+4].[O-2].ClCCl | null | 16 | OCc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>[O-2].[Mn+4].[O-2].ClCCl>O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-729e14f27bc94bc7b5b3ec587e691c03 | CCN(CC)C(=O)CCl.CCOC(=O)c1cc2cc(O)ccc2[nH]1>>CCOC(=O)c1cc2cc(OCC(=O)N(CC)CC)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)O.ClCC(=O)N(CC)CC.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(N(CC)CC)=O | Cl[CH2:12][C:13](=[O:14])[N:15]([CH2:16][CH3:17])[CH2:18][CH3:19].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[cH:20][cH:21][c:22]2[nH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH2:12][C:13](=[O:14])[N:15]([CH2:16][CH3:17])[CH2:18][CH3:19])[cH:20][cH:21][c:22... | CCN(CC)C(=O)CCl.CCOC(=O)c1cc2cc(O)ccc2[nH]1 | CCOC(=O)c1cc2cc(OCC(=O)N(CC)CC)ccc2[nH]1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2[nH]ccc2c1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[#7:4](-[C:6])-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 32.7 | [{"value": 32.7, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)OCC(N(CC)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A mixture of 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (1 g, 5 mmol), 2-chloro-N,N-diethylacetamide (1 mL, 7.5 mmol) and cesium carbonate (5 g, 15 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 6 hours. The reaction was diluted with ethyl acetate (160 mL), washed with water (5×50 mL) and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 6 | CCN(CC)C(=O)CCl.CCOC(=O)c1cc2cc(O)ccc2[nH]1>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)c1cc2cc(OCC(=O)N(CC)CC)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16b86cd36dd247ae86be41aa20a89b40 | CCOC(=O)c1cc2cc(CCCN(CC)CC)ccc2[nH]1>>CCN(CC)CCCc1ccc2[nH]c(CO)cc2c1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCCN(CC)CC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)N(CCCC=1C=C2C=C(NC2=CC1)CO)CC | CCO[C:15]([c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:19][c:18]2[cH:17]1)=[O:16]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][c:14]([CH2:15][OH:16])[cH:17][c:18]2[cH:19]1 | CCOC(=O)c1cc2cc(CCCN(CC)CC)ccc2[nH]1 | CCN(CC)CCCc1ccc2[nH]c(CO)cc2c1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2[nH]ccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 66 | [{"value": 66.0, "product": "C(C)N(CCCC=1C=C2C=C(NC2=CC1)CO)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "C(C)N(CCCC=1C=C2C=C(NC2=CC1)CO)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 5-(3-Diethylamino-propyl)-1H-indole-2-carboxylic acid ethyl ester (1.2 g, 3.97 mmol) in tetrahydrofuran (48 mL) was added dropwise to the lithium aluminum hydride (602 mg, 15.87 mmol) stirred in tetrahydrofuran (30 mL) under nitrogen. After stirring for 2 hours, the reaction was quenched in water (0.6 mL), 15% sodium h... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2[nH]ccc2c1 | HO- | O1CCCC1 | null | 2 | CCOC(=O)c1cc2cc(CCCN(CC)CC)ccc2[nH]1>O1CCCC1>CCN(CC)CCCc1ccc2[nH]c(CO)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56203688914142008e972e12feb5d588 | CCN(CC)CCCc1ccc2[nH]c(CO)cc2c1>>CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1 | C(C)N(CCCC=1C=C2C=C(NC2=CC1)CO)CC>>C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][c:14]([CH2:15][OH:16])[cH:17][c:18]2[cH:19]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][c:14]([CH:15]=[O:16])[cH:17][c:18]2[cH:19]1 | CCN(CC)CCCc1ccc2[nH]c(CO)cc2c1 | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1 | null | [O-2].[Mn+2] | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2[nH]ccc2c1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 86.1 | [{"value": 83.0, "product": "C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.1, "product": "C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Manganese oxide (3.75 g, 43.1 mmol) was added portionwise to [5-(3-diethylamino-propyl)-1H-indol-2-yl]-methanol (660 mg, 2.53 mmol) dissolved in dichloromethane (68 mL) under nitrogen at room temperature. The precipitate was filtered through celite, washing with hot dichloromethane. The filtrate was concentrated to giv... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2[nH]ccc2c1 | null | [O-2].[Mn+2].ClCCl | null | null | CCN(CC)CCCc1ccc2[nH]c(CO)cc2c1>[O-2].[Mn+2].ClCCl>CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5d90ecbecc8a47c082a6f9375dee9fa9 | C=CC(=O)OC(C)(C)C.CCOC(=O)c1cc2cc(Br)ccc2[nH]1>>CCOC(=O)c1cc2cc(C=CC(=O)OC(C)(C)C)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)Br.C(C=C)(=O)OC(C)(C)C.C(C)N(CC)CC.O>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)C=CC(=O)OC(C)(C)C | [CH2:11]=[CH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].Br[c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:23][c:22]2[cH:21][cH:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([CH:11]=[CH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21][c:... | C=CC(=O)OC(C)(C)C.CCOC(=O)c1cc2cc(Br)ccc2[nH]1 | CCOC(=O)c1cc2cc(C=CC(=O)OC(C)(C)C)ccc2[nH]1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | ClCCl.C(C)(=O)O | C-C Coupling | Heck terminal vinyl | 83e0d899ed3e8e4a95a3a6dff95d3a360d67b1a2707c2df30c2396604bf526cb | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccc2[nH]ccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]=[CH2;D1;+0:16]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[CH;D2;+0:16]=[C:15]-[C:13](=[O;D1;H0:14])-[#8:12]-[C:9](-[C;D1;H3:8])(-[C;D1;H3:10])-[C;D1;H3:11]):[c:7]:[c:6]:1 | 28.5 | [{"value": 28.0, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)C=CC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.5, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)C=CC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of 5-bromoindole-2-carboxylic acid ethyl ester (2.68 g, 10 mmol), tert-butyl acrylate (4.4 mL, 30 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.7 g, 1 mmol) and triethylamine (17 mL) in acetic acid (17 mL) was heated at 120° C. in a closed vessel for 6 hrs. The cooled reaction mixture was poured i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.ClCCl.C(C)(=O)O | 120 | null | C=CC(=O)OC(C)(C)C.CCOC(=O)c1cc2cc(Br)ccc2[nH]1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.ClCCl.C(C)(=O)O>CCOC(=O)c1cc2cc(C=CC(=O)OC(C)(C)C)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c4be958a7e04d0b8f5ca4b6d43fa9a7 | CCOC(=O)c1cc2cc(C=CC(=O)OC(C)(C)C)ccc2[nH]1>>CCOC(=O)c1cc2cc(CCC(=O)OC(C)(C)C)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)C=CC(=O)OC(C)(C)C>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(=O)OC(C)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([CH:11]=[CH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21][c:22]2[nH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([CH2:11][CH2:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21][c:22]... | CCOC(=O)c1cc2cc(C=CC(=O)OC(C)(C)C)ccc2[nH]1 | CCOC(=O)c1cc2cc(CCC(=O)OC(C)(C)C)ccc2[nH]1 | null | [Pd] | CO.C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccc2[nH]ccc2c1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12] | 100.8 | [{"value": 99.0, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.8, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-(2-tert-butoxycarbonyl-vinyl)-1H-indole-2-carboxylic acid ethyl ester (1.6 g, 5 mmol) in ethyl acetate (40 mL) and methanol (80 mL) was hydrogenated over 5% palladium on carbon (0.2 g) at room temperature for overnight. The catalyst was filtered off and the filtrate was concentrated to give 1.6 g (99%) ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccc2[nH]ccc2c1 | null | [Pd].CO.C(C)(=O)OCC | null | null | CCOC(=O)c1cc2cc(C=CC(=O)OC(C)(C)C)ccc2[nH]1>[Pd].CO.C(C)(=O)OCC>CCOC(=O)c1cc2cc(CCC(=O)OC(C)(C)C)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-27b8a00e9c0d4898a7d3433761debdbe | CCOC(=O)c1cc2cc(CCC(=O)OC(C)(C)C)ccc2[nH]1>>CCOC(=O)c1cc2cc(CCC(=O)O)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(=O)O | CC(C)(C)[O:15][C:13]([CH2:12][CH2:11][c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:19][c:18]2[cH:17][cH:16]1)=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([CH2:11][CH2:12][C:13](=[O:14])[OH:15])[cH:16][cH:17][c:18]2[nH:19]1 | CCOC(=O)c1cc2cc(CCC(=O)OC(C)(C)C)ccc2[nH]1 | CCOC(=O)c1cc2cc(CCC(=O)O)ccc2[nH]1 | null | null | ClCCl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccc2[nH]ccc2c1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 99.5 | [{"value": 99.0, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.5, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-(2-tert-butoxycarbonyl-ethyl)-1H-indole-2-carboxylic acid ethyl ester (1.6 g, 5 mmol) in dichloromethane (12 mL) was added 8 mL of 40% trifluoroacetic acid. The mixture was stirred at room temperature for 1 hour. The reaction was concentrated, dissolved in toluene, concentrate, dissolved in dichlorom... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1 | Other | ClCCl | null | 1 | CCOC(=O)c1cc2cc(CCC(=O)OC(C)(C)C)ccc2[nH]1>ClCCl>CCOC(=O)c1cc2cc(CCC(=O)O)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d8cdb2203d74f76a8b987eed19fa197 | C1CCNC1.CCOC(=O)c1cc2cc(CCC(=O)O)ccc2[nH]1>>CCOC(=O)c1cc2cc(CCC(=O)N3CCCC3)ccc2[nH]1 | N1CCCC1.C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(N1CCCC1)=O | [NH:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1.O[C:13]([CH2:12][CH2:11][c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:23][c:22]2[cH:21][cH:20]1)=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([CH2:11][CH2:12][C:13](=[O:14])[N:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20][cH:21][c... | C1CCNC1.CCOC(=O)c1cc2cc(CCC(=O)O)ccc2[nH]1 | CCOC(=O)c1cc2cc(CCC(=O)N3CCCC3)ccc2[nH]1 | null | null | ClCCl.CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCc1ccc2[nH]ccc2c1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | 95.4 | [{"value": 95.0, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(N1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(N1CCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 5-(2-carboxy-ethyl)-1H-indole-2-carboxylic acid ethyl ester (1.3 g, 5 mmol) in 10 mL of dimethylformamide, was added 1,1′-carbonyldiimidazole (973 mg, 6 mmol). The mixture was stirred under nitrogen at room temperature for 30 mins. To the reaction mixture was added pyrrolidine (1.3 mL, 15 mmol) dropwis... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | ClCCl.CN(C=O)C | null | 0.5 | C1CCNC1.CCOC(=O)c1cc2cc(CCC(=O)O)ccc2[nH]1>ClCCl.CN(C=O)C>CCOC(=O)c1cc2cc(CCC(=O)N3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-96215529b7e347b4ac76b99153d11260 | CCOC(=O)c1cc2cc(CCC(=O)N3CCCC3)ccc2[nH]1>>OCc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | C(C)OC(=O)C=1NC2=CC=C(C=C2C1)CCC(N1CCCC1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)CO | CCO[C:2](=[O:1])[c:3]1[cH:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][C:10](=O)[N:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17][c:18]2[nH:19]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17][c:18]2[nH:19]1 | CCOC(=O)c1cc2cc(CCC(=O)N3CCCC3)ccc2[nH]1 | OCc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | null | null | O1CCCC1 | Reduction | OtherReaction | c69e55c870fca7a48716cf1a13d3b1c66b1429a862fb2c663e47b4c648179c46 | a65143cb02ef97811e30a8153880ab0c649a356c31e2df2bd3a78b2a9b48cbfc | c1cc2cc(CCCN3CCCC3)ccc2[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].O=[C;H0;D3;+0:7](-[C:8]-[C:9])-[#7:10](-[C:11])-[C:12]>>[C:11]-[#7:10](-[CH2;D2;+0:7]-[C:8]-[C:9])-[C:12].[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 78 | [{"value": 78.0, "product": "N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 5-(3-oxo-3-pyrrolidin-1-yl-propyl)-1H-indole-2-carboxylic acid ethyl ester (1.5 g, 4.8 mmol) in 100 mL of tetrahydrofuran, lithium aluminum hydride powder (728 mg, 19.2 mmol) was added. The mixture was stirred under nitrogen at room temperature for 2 hour. To the reaction mixture was added water (0.75 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide | Primary alcohol | null | null | c1ccc2[nH]ccc2c1.C1CC[NH]C1 | Other | O1CCCC1 | null | 2 | CCOC(=O)c1cc2cc(CCC(=O)N3CCCC3)ccc2[nH]1>O1CCCC1>OCc1cc2cc(CCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-231664bc14de4d499818d613c868b825 | OCc1cc2cc(CCCN3CCCC3)ccc2[nH]1>>O=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)CO>>N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)C=O | [OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17][c:18]2[nH:19]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17][c:18]2[nH:19]1 | OCc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | O=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | null | [O-2].[Mn+4].[O-2] | ClCCl.C1(=CC=CC=C1)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1cc2cc(CCCN3CCCC3)ccc2[nH]1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 72.6 | [{"value": 72.0, "product": "N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Manganese (IV) oxide (4.7 g, 54 mmol) was added to a mixture of [5-(3-pyrrolidin-1-yl-propyl)-1H-indol-2-yl]-methanol (940 mg, 3.6 mmol) in dichloromethane (150 mL) and toluene (150 mL). The mixture was stirred at room temperature for overnight. The reaction was filtered through a pad of celite and the filtrate was con... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2[nH]ccc2c1.C1CC[NH]C1 | null | [O-2].[Mn+4].[O-2].ClCCl.C1(=CC=CC=C1)C | null | 8 | OCc1cc2cc(CCCN3CCCC3)ccc2[nH]1>[O-2].[Mn+4].[O-2].ClCCl.C1(=CC=CC=C1)C>O=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fdf0c9ee64b413fab01051ace62c757 | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccccc2N1>>CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4ccccc43)cc2c1 | N1C(CC2=CC=CC=C12)=O.C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=O)CC.N1CCCCC1>>C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O)CC | O=[CH:15][c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:28][c:27]2[cH:26]1.[CH2:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][c:14]([CH:15]=[C:16]3[C... | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccccc2N1 | CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4ccccc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 18.3 | [{"value": 18.0, "product": "C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.3, "product": "C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A mixture of oxindole (26 mg, 0.19 mmol), 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde (50 mg, 0.19 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated in a sealed tube at 95° C. for 20 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 13 mg (18%) of the title... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | C(C)O | 95 | null | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccccc2N1>C(C)O>CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4ccccc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3f636c0e24cc43d8915a9f71c967d359 | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(Br)ccc2N1>>CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4ccc(Br)cc43)cc2c1 | BrC=1C=C2CC(NC2=CC1)=O.C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=O)CC.N1CCCCC1>>BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)CCCN(CC)CC | O=[CH:15][c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:29][c:28]2[cH:27]1.[CH2:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23]([Br:24])[cH:25][c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][c:14]([CH:15]=[... | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(Br)ccc2N1 | CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4ccc(Br)cc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 60.5 | [{"value": 59.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)CCCN(CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.5, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)CCCN(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A mixture of 5-bromo-2-oxindole (41 mg, 0.19 mmol), 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde (50 mg, 0.19 mmol) and piperidine(0.1 mL) in ethanol (1 mL) was heated in a sealed tube at 95° C. for 20 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 52 mg (59%) of ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | C(C)O | 95 | null | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(Br)ccc2N1>C(C)O>CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4ccc(Br)cc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e0c06de60a0f4dbdbbee86bcceb20414 | C1CCNCC1.CCO.O=C1Cc2ccc(-c3ccccc3)cc2N1>>CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4cc(-c5ccccc5)ccc43)cc2c1 | C1(=CC=CC=C1)C1=CC=C2CC(NC2=C1)=O.N1CCCCC1.C(C)O>>C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O)CC | [NH:3]1[CH2:6][CH2:7][CH2:9][CH2:10][CH2:11]1.O[CH2:2][CH3:1].[cH:4]1[cH:26][cH:25][cH:24][c:23](-[c:22]2[cH:21][c:20]3[c:31]([cH:30][cH:29]2)[CH2:16][C:17](=[O:18])[NH:13]3)[cH:28]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][c:14]([CH:15]=[C:16]3[C:17](=[O:18])[NH:19][c... | C1CCNCC1.CCO.O=C1Cc2ccc(-c3ccccc3)cc2N1 | CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4cc(-c5ccccc5)ccc43)cc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 089dacf1f101b3338c76329ce8108f3bb791564c06e8cdc2b2d789e56b83861a | 535a0a614ca7eb7ad9fd9193d1a124f509dd520a848d242a9477312b6cced420 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2ccccc2[nH]1 | O-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[NH;D2;+0:8]-1.[O;D1;H0:9]=[C;H0;D3;+0:10]1-[CH2;D2;+0:11]-[c:12](:[c:13]):[c;H0;D3;+0:14](:[c:15]:[c:16]-[c:17]2:[c:18]:[c:19]:[cH;D2;+0:20]:[cH;D2;+0:21]:[cH;D2;+0:22]:2)-[NH;D2;+0:23]-1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8... | 56 | [{"value": 56.0, "product": "C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O)CC", "details": "PERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A mixture of 6-phenyl-2-oxindole (41 mg, 0.19 mmol) 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde (50 mg, 0.19 mmol) and piperidine(0.1 mL) in ethanol (1 mL) was heated in a sealed tube at 95° C. for 20 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 49 mg (56%) of ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary alcohol.Secondary amine | Secondary amide.Tertiary amine | C1CCNCC1.c1ccccc1.c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2.c1ccccc1 | null | null | 95 | null | C1CCNCC1.CCO.O=C1Cc2ccc(-c3ccccc3)cc2N1>>CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4cc(-c5ccccc5)ccc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53061c6f3f294badb4816a1db9132bb0 | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(-c3ccccc3)ccc2N1>>CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4ccc(-c5ccccc5)cc43)cc2c1 | C1(=CC=CC=C1)C=1C=C2CC(NC2=CC1)=O.C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=O)CC.N1CCCCC1>>C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)C1=CC=CC=C1)=O)CC | O=[CH:15][c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:34][c:33]2[cH:32]1.[CH2:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][c:31]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10]... | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(-c3ccccc3)ccc2N1 | CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4ccc(-c5ccccc5)cc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(-c3ccccc3)cc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 11.7 | [{"value": 11.0, "product": "C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)C1=CC=CC=C1)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.7, "product": "C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)C1=CC=CC=C1)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A mixture of 5-phenyl-2-oxindole (41 mg, 0.19 mmol), 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde (50 mg, 0.19 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated in a sealed tube at 95° C. for 20 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 10 mg (11%) o... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2.c1ccccc1 | HO- | C(C)O | 95 | null | CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(-c3ccccc3)ccc2N1>C(C)O>CCN(CC)CCCc1ccc2[nH]c(C=C3C(=O)Nc4ccc(-c5ccccc5)cc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2c7d67387e24d559111e2a7f2c314a1 | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(-c3ccccc3)ccc2N1>>CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(-c5ccccc5)cc43)cc2c1 | C1(=CC=CC=C1)C=1C=C2CC(NC2=CC1)=O.CN(CCOC=1C=C2C=C(NC2=CC1)C=O)C.N1CCCCC1>>CN(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)C1=CC=CC=C1)=O)C | O=[CH:13][c:12]1[nH:11][c:10]2[cH:9][cH:8][c:7]([O:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[cH:32][c:31]2[cH:30]1.[CH2:14]1[C:15](=[O:16])[NH:17][c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][c:29]21>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]2[nH:11][c:12]([CH:13]=... | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(-c3ccccc3)ccc2N1 | CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(-c5ccccc5)cc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(-c3ccccc3)cc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 68.5 | [{"value": 68.0, "product": "CN(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)C1=CC=CC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "CN(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)C1=CC=CC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 5-phenyl-2-oxindole (41 mg, 0.2 mmol), 5-(2-dimethylamino-ethoxy)-1H-indole-2-carbaldehyde (46 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 58 mg (68%) of the title compou... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2.c1ccccc1 | HO- | C(C)O | 100 | null | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(-c3ccccc3)ccc2N1>C(C)O>CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(-c5ccccc5)cc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-198c5c247e6e48a1ae97332765a7b4a4 | O=C1Cc2cc(-c3ccccc3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(-c3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | C1(=CC=CC=C1)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>C1(=CC=CC=C1)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[cH:14][c:15]2[CH2:16]1.O=[CH:17][c:18]1[cH:19][c:20]2[cH:21][c:22]([O:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[nH:34]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:... | O=C1Cc2cc(-c3ccccc3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(-c3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(-c3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 61 | [{"value": 61.0, "product": "C1(=CC=CC=C1)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "C1(=CC=CC=C1)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 5-phenyl-2-oxindole (23 mg, 0.11 mmol), 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde (29 mg, 0.11 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 30 mg (61%) of the title co... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | C(C)O | 100 | null | O=C1Cc2cc(-c3ccccc3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>C(C)O>O=C1Nc2ccc(-c3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a2cde4a8f18426c9900acdda16e3e42 | O=C1Cc2ccccc2N1.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>>O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | N1C(CC2=CC=CC=C12)=O.N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10]1.O=[CH:11][c:12]1[cH:13][c:14]2[cH:15][c:16]([O:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[cH:26][cH:27][c:28]2[nH:29]1>>[O: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][c:14]2[cH:15][c:16]([O:17][C... | O=C1Cc2ccccc2N1.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 95 | [{"value": 95.0, "product": "N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 2-oxindole (29 mg, 0.22 mmol), 5-(2-morpholin-4-yl-ethoxy)-1H-indole-2-carbaldehyde (60 mg, 0.22 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 81 mg (95%) of the title compound as ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1COCC[NH]1 | HO- | C(C)O | 100 | null | O=C1Cc2ccccc2N1.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>C(C)O>O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d936a1abf684c14a8743006197b021c | O=C1Cc2cc(Br)ccc2N1.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>>O=C1Nc2ccc(Br)cc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | BrC=1C=C2CC(NC2=CC1)=O.N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCOCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[CH2:11]1.O=[CH:12][c:13]1[cH:14][c:15]2[cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[cH:27][cH:28][c:29]2[nH:30]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[C:11]1=[CH:12][c:13]1[cH:14][c:15]2[cH:16... | O=C1Cc2cc(Br)ccc2N1.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | O=C1Nc2ccc(Br)cc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 64 | [{"value": 64.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.1, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 5-bromo-2-oxindole (46 mg, 0.22 mmol), 5-(2-morpholin-4-yl-ethoxy)-1H-indole-2-carbaldehyde (60 mg, 0.22 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 65 mg (64%) of the title comp... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1COCC[NH]1 | HO- | C(C)O | 100 | null | O=C1Cc2cc(Br)ccc2N1.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>C(C)O>O=C1Nc2ccc(Br)cc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4eee7e344c234cb390917980c4842a84 | O=C1Cc2ccc(-c3ccccc3)cc2N1.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>>O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | C1(=CC=CC=C1)C1=CC=C2CC(NC2=C1)=O.N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[cH:13][cH:14][c:15]2[CH2:16]1.O=[CH:17][c:18]1[cH:19][c:20]2[cH:21][c:22]([O:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[cH:32][cH:33][c:34]2[nH:35]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:1... | O=C1Cc2ccc(-c3ccccc3)cc2N1.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 71.6 | [{"value": 71.0, "product": "N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.6, "product": "N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 6-phenyl-2-oxindole (44 mg, 0.21 mmol), 5-(2-morpholin-4-yl-ethoxy)-1H-indole-2-carbaldehyde (58 mg, 0.21 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 70 mg (71%) of the title com... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccc2[nH]ccc2c1.C1COCC[NH]1 | HO- | C(C)O | 100 | null | O=C1Cc2ccc(-c3ccccc3)cc2N1.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>C(C)O>O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5613d7906dbc41708c93702a7c443c0b | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccccc2N1>>CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccccc43)cc2c1 | N1C(CC2=CC=CC=C12)=O.CN(CCOC=1C=C2C=C(NC2=CC1)C=O)C.N1CCCCC1>>CN(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O)C | O=[CH:13][c:12]1[nH:11][c:10]2[cH:9][cH:8][c:7]([O:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[cH:26][c:25]2[cH:24]1.[CH2:14]1[C:15](=[O:16])[NH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]2[nH:11][c:12]([CH:13]=[C:14]3[C:15](=[O:16])[NH:17][c:18]4[cH:19][c... | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccccc2N1 | CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccccc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 80.9 | [{"value": 79.0, "product": "CN(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "CN(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of oxindole (28 mg, 0.216 mmol), 5-(2-dimethylamino-ethoxy)-1H-indole-2-carbaldehyde (50 mg, 0.21 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 59 mg (79%) of the title compound as an... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | C(C)O | 100 | null | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccccc2N1>C(C)O>CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccccc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3515eaf7aaae4663a11dd8cca09db1cc | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(Br)ccc2N1>>CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(Br)cc43)cc2c1 | BrC=1C=C2CC(NC2=CC1)=O.CN(CCOC=1C=C2C=C(NC2=CC1)C=O)C.N1CCCCC1>>BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN(C)C | O=[CH:13][c:12]1[nH:11][c:10]2[cH:9][cH:8][c:7]([O:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[cH:27][c:26]2[cH:25]1.[CH2:14]1[C:15](=[O:16])[NH:17][c:18]2[cH:19][cH:20][c:21]([Br:22])[cH:23][c:24]21>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]2[nH:11][c:12]([CH:13]=[C:14]3[C:15](=[O:16])[NH:17][c:18]4[... | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(Br)ccc2N1 | CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(Br)cc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 80.4 | [{"value": 78.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 5-bromo-2-oxindole (46 mg, 0.215 mmol), 5-(2-dimethylamino-ethoxy)-1H-indole-2-carbaldehyde (50 mg, 0.21 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 72 mg (78%) of the title comp... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | C(C)O | 100 | null | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(Br)ccc2N1>C(C)O>CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(Br)cc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-698a58a55e504e8e99da50ff8efd676e | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccc(-c3ccccc3)cc2N1>>CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4cc(-c5ccccc5)ccc43)cc2c1 | C1(=CC=CC=C1)C1=CC=C2CC(NC2=C1)=O.CN(CCOC=1C=C2C=C(NC2=CC1)C=O)C.N1CCCCC1>>CN(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O)C | O=[CH:13][c:12]1[nH:11][c:10]2[cH:9][cH:8][c:7]([O:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[cH:32][c:31]2[cH:30]1.[CH2:14]1[C:15](=[O:16])[NH:17][c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[cH:27][cH:28][c:29]21>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]2[nH:11][c:12]([CH:13]=... | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccc(-c3ccccc3)cc2N1 | CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4cc(-c5ccccc5)ccc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 76.5 | [{"value": 76.0, "product": "CN(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.5, "product": "CN(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 6-phenyl-2-oxindole (45 mg, 0.21 mmol), 5-(2-dimethylamino-ethoxy)-1H-indole-2-carbaldehyde (50 mg, 0.21 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 68 mg (76%) of the title comp... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2.c1ccccc1 | HO- | C(C)O | 100 | null | CN(C)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccc(-c3ccccc3)cc2N1>C(C)O>CN(C)CCOc1ccc2[nH]c(C=C3C(=O)Nc4cc(-c5ccccc5)ccc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9af4201e7c44069a5c4367b563b8b0a | O=C1Cc2ccccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | N1C(CC2=CC=CC=C12)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10]1.O=[CH:11][c:12]1[cH:13][c:14]2[cH:15][c:16]([O:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[cH:25][cH:26][c:27]2[nH:28]1>>[O: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][c:14]2[cH:15][c:16]([O:17][CH2:18]... | O=C1Cc2ccccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 81.7 | [{"value": 81.0, "product": "N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of oxindole (26.6 mg, 0.2 mmol), 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde (52 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 61 mg (81%) of the title compound.
Con... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | C(C)O | 100 | null | O=C1Cc2ccccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>C(C)O>O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de55be6c638c4f83869efa1708c29f03 | O=C1Cc2cc(Br)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(Br)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | BrC=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[CH2:11]1.O=[CH:12][c:13]1[cH:14][c:15]2[cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][cH:27][c:28]2[nH:29]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[C:11]1=[CH:12][c:13]1[cH:14][c:15]2[cH:16][c:17... | O=C1Cc2cc(Br)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(Br)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 80 | [{"value": 80.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.6, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 5-bromo-2-oxindole (42 mg, 0.2 mmol), 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde (52 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 72 mg (80%) of the title compo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | C(C)O | 100 | null | O=C1Cc2cc(Br)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>C(C)O>O=C1Nc2ccc(Br)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-08676a73bb6041e6a2e4ec36154988e9 | O=C1Cc2ccc(-c3ccccc3)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | C1(=CC=CC=C1)C1=CC=C2CC(NC2=C1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>C1(=CC=CC=C1)C1=CC=C2C(C(NC2=C1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[cH:13][cH:14][c:15]2[CH2:16]1.O=[CH:17][c:18]1[cH:19][c:20]2[cH:21][c:22]([O:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[nH:34]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:... | O=C1Cc2ccc(-c3ccccc3)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 72.3 | [{"value": 72.0, "product": "C1(=CC=CC=C1)C1=CC=C2C(C(NC2=C1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.3, "product": "C1(=CC=CC=C1)C1=CC=C2C(C(NC2=C1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 6-phenyl-2-oxindole (41 mg, 0.2 mmol), 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde (50 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 65 mg (72%) of the title comp... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | C(C)O | 100 | null | O=C1Cc2ccc(-c3ccccc3)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>C(C)O>O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4463797a305e471cbbc91851dbd5a66e | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccccc2N1>>CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccccc43)cc2c1 | N1C(CC2=CC=CC=C12)=O.C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=O)CC.N1CCCCC1>>C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O)CC | O=[CH:15][c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:28][c:27]2[cH:26]1.[CH2:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][c:14]([CH:15]=[C:16]3[C:17]... | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccccc2N1 | CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccccc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 67 | [{"value": 67.0, "product": "C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of oxindole (26 mg, 0.2 mmol), 5-(2-diethylamino-ethoxy)-1H-indole-2-carbaldehyde (50 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 50 mg (67%) of the title compound.
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | C(C)O | 100 | null | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccccc2N1>C(C)O>CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccccc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4ce0a9daf4049f5b9f6b6e8d5d0e79e | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(Br)ccc2N1>>CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(Br)cc43)cc2c1 | BrC=1C=C2CC(NC2=CC1)=O.C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=O)CC.N1CCCCC1>>BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN(CC)CC | O=[CH:15][c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:29][c:28]2[cH:27]1.[CH2:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23]([Br:24])[cH:25][c:26]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][c:14]([CH:15]=[C:16... | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(Br)ccc2N1 | CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(Br)cc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 66 | [{"value": 66.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN(CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "BrC=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 5-bromo-2-oxindole (41 mg, 0.2 mmol), 5-(2-diethylamino-ethoxy)-1H-indole-2-carbaldehyde (50 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 60 mg (66%) of the title compound... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | C(C)O | 100 | null | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(Br)ccc2N1>C(C)O>CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(Br)cc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-537ab0e93e8849b8a56685bcf8ec77a6 | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccc(-c3ccccc3)cc2N1>>CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4cc(-c5ccccc5)ccc43)cc2c1 | C1(=CC=CC=C1)C1=CC=C2CC(NC2=C1)=O.C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=O)CC.N1CCCCC1>>C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O)CC | O=[CH:15][c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:34][c:33]2[cH:32]1.[CH2:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][c:22](-[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][cH:30][c:31]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:... | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccc(-c3ccccc3)cc2N1 | CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4cc(-c5ccccc5)ccc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 72 | [{"value": 72.0, "product": "C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC(=CC=C12)C1=CC=CC=C1)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 6-phenyl-2-oxindole (40.5 mg, 0.2 mmol), 5-(2-diethylamino-ethoxy)-1H-indole-2-carbaldehyde (50 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 65 mg (72%) of the title compo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2.c1ccccc1 | HO- | C(C)O | 100 | null | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2ccc(-c3ccccc3)cc2N1>C(C)O>CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4cc(-c5ccccc5)ccc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-43bbeb0308db46c6a1084da79f6862e9 | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(-c3ccccc3)ccc2N1>>CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(-c5ccccc5)cc43)cc2c1 | C1(=CC=CC=C1)C=1C=C2CC(NC2=CC1)=O.C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=O)CC.N1CCCCC1>>C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)C1=CC=CC=C1)=O)CC | O=[CH:15][c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:34][c:33]2[cH:32]1.[CH2:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][c:31]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:... | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(-c3ccccc3)ccc2N1 | CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(-c5ccccc5)cc43)cc2c1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(-c3ccccc3)cc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 54.1 | [{"value": 54.0, "product": "C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)C1=CC=CC=C1)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.1, "product": "C(C)N(CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)C1=CC=CC=C1)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 5-phenyl-2-oxindole (39 mg, 0.18 mmol), 5-(2-diethylamino-ethoxy)-1H-indole-2-carbaldehyde (48 mg, 0.18 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 44 mg (54%) of the title compo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2.c1ccccc1 | HO- | C(C)O | 100 | null | CCN(CC)CCOc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(-c3ccccc3)ccc2N1>C(C)O>CCN(CC)CCOc1ccc2[nH]c(C=C3C(=O)Nc4ccc(-c5ccccc5)cc43)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6a751a881f624fc197019392a7837fb0 | O=C1Cc2ccccc2N1.O=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccccc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | N1C(CC2=CC=CC=C12)=O.N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10]1.O=[CH:11][c:12]1[cH:13][c:14]2[cH:15][c:16]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[cH:25][cH:26][c:27]2[nH:28]1>>[O: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][c:14]2[cH:15][c:16]([CH2:17][CH2... | O=C1Cc2ccccc2N1.O=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccccc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 74 | [{"value": 74.0, "product": "N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of oxindole (27 mg, 0.2 mmol), 5-(3-pyrrolidin-1-yl-propyl)-1H-indole-2-carbaldehyde (51 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated in a sealed tube at 80° C. for 3 hours. The precipitate was collected by vacuum filtration, washed with ethanol/ethyl acetate and dried to give 55 mg (74%... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | C(C)O | 80 | null | O=C1Cc2ccccc2N1.O=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1>C(C)O>O=C1Nc2ccccc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c550b8fc70904b66b7a429d15322bdd5 | O=C1Cc2cc(C(=O)O)ccc2N1.O=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(C(=O)O)cc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | C(=O)(O)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCCC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>O=C1NC2=CC=C(C=C2C1=CC=1NC2=CC=C(C=C2C1)CCCN1CCCC1)C(=O)O | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[CH2:13]1.O=[CH:14][c:15]1[cH:16][c:17]2[cH:18][c:19]([CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[nH:31]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[C:13]1=[CH:14][... | O=C1Cc2cc(C(=O)O)ccc2N1.O=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(C(=O)O)cc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | 80 | CELSIUS | null | null | A mixture of 5-carboxy-2-oxindole (35 mg, 0.2 mmol), 5-(3-pyrrolidin-1-yl-propyl)-1H-indole-2-carbaldehyde (51 mg, 0.2 mmol) and piperidine (0.2 mL) in ethanol (1 mL) was heated in a sealed tube at 80° C. for 6 hours. The reaction mixture was concentrated and the residue was dissolved in methanol, made acidic with 1 N ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | C(C)O | 80 | null | O=C1Cc2cc(C(=O)O)ccc2N1.O=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1>C(C)O>O=C1Nc2ccc(C(=O)O)cc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f579a24fb5e4ee5a5f70e5cfc3fa5ac | C1CCNCC1.CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(C(=O)O)ccc2N1>>O=C1Nc2ccc(C(=O)O)cc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | Cl.C(=O)(O)C=1C=C2CC(NC2=CC1)=O.C(C)N(CCCC=1C=C2C=C(NC2=CC1)C=O)CC.N1CCCCC1>>O=C1NC2=CC=C(C=C2C1=CC=1NC2=CC=C(C=C2C1)CCCN1CCCC1)C(=O)O | C1C[CH2:25][CH2:26][CH2:27]N1.CC[N:23]([CH2:22][CH2:21][CH2:20][c:19]1[cH:18][c:17]2[cH:16][c:15]([CH:14]=O)[nH:31][c:30]2[cH:29][cH:28]1)[CH2:24]C.[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[CH2:13]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[C:13]1... | C1CCNCC1.CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(C(=O)O)ccc2N1 | O=C1Nc2ccc(C(=O)O)cc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 99aa3ae843496898b1ed11db7711d26dc1e07304bd6d13d085ff7297fd81b52b | 3cf6662b068357c114d90840666efe4f8d673999a867765d8ab894670435e08f | O=C1Nc2ccccc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 | C-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[CH2;D2;+0:4]-C.O=[CH;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9].C1-C-[CH2;D2;+0:10]-[C:11]-[CH2;D2;+0:12]-N-1.[O;D1;H0:13]=[C:14]1-[#7:15]-[c:16]:[c:17](:[c:18])-[CH2;D2;+0:19]-1>>[C:3]-[C:2]-[N;H0;D3;+0:1]1-[CH2;D2;+0:4]-[CH2;D2;+0:10]-[C:11]-[CH2;D2;+0:12]-1.[O;D1;H0:13]=[C:14]1-[#7:15]-[... | null | [] | 80 | CELSIUS | null | null | A mixture of 5-carboxy-2-oxindole (35 mg, 0.2 mmol), 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde (51 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 80° C. for 6 hours. The reaction was acidified with 1 N HCl and the precipitate was collected by vacuum filtration, washed with 1 N HCl, water... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine.Tertiary amine | Tertiary amine | C1CCNCC1.c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.C1CC[NH]C1 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | C(C)O | 80 | null | C1CCNCC1.CCN(CC)CCCc1ccc2[nH]c(C=O)cc2c1.O=C1Cc2cc(C(=O)O)ccc2N1>C(C)O>O=C1Nc2ccc(C(=O)O)cc2C1=Cc1cc2cc(CCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-062b05b58d5c416ea8ee5f2abff199eb | O=C1Cc2cc(C(=O)O)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(C(=O)O)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1NC2=CC=C(C=C2C1)C(=O)O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>O=C1NC2=CC=C(C=C2C1=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1)C(=O)O | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[CH2:13]1.O=[CH:14][c:15]1[cH:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[nH:31]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[C:13]1=[CH:14][c:... | O=C1Cc2cc(C(=O)O)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(C(=O)O)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2-Oxo-2,3-dihydro-1H-indole-5-carboxylic acid was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2cc(C(=O)O)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(C(=O)O)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-90555757d2d44d1c82b81f30f9bf253e | O=C1Cc2ccc(C(=O)O)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2cc(C(=O)O)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1NC2=CC(=CC=C2C1)C(=O)O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>O=C1NC2=CC(=CC=C2C1=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1)C(=O)O | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][cH:11][c:12]2[CH2:13]1.O=[CH:14][c:15]1[cH:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[nH:31]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][cH:11][c:12]2[C:13]1=[CH:14][c:... | O=C1Cc2ccc(C(=O)O)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2cc(C(=O)O)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2ccc(C(=O)O)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2cc(C(=O)O)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-21c464a4d863490dbf489ffc0acbc4dd | O=C1Cc2c(CCO)cccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2cccc(CCO)c2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | OCCC1=C2CC(NC2=CC=C1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>OCCC1=C2C(C(NC2=CC=C1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH2:9][CH2:10][OH:11])[c:12]2[CH2:13]1.O=[CH:14][c:15]1[cH:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[nH:31]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH2:9][CH2:10][OH:11])[c:12]2[C:13]1=[CH:14][... | O=C1Cc2c(CCO)cccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2cccc(CCO)c2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 4-(2-Hydroxy-ethyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2c(CCO)cccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2cccc(CCO)c2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ee2e71e16ab1486fb3c78684718aaabe | O=C1Cc2ccc(-c3cccnc3)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2cc(-c3cccnc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | N1=CC(=CC=C1)C1=CC=C2CC(NC2=C1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>N1=CC(=CC=C1)C1=CC=C2C(C(NC2=C1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][n:11][cH:12]3)[cH:13][cH:14][c:15]2[CH2:16]1.O=[CH:17][c:18]1[cH:19][c:20]2[cH:21][c:22]([O:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[nH:34]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][n:11][cH:12... | O=C1Cc2ccc(-c3cccnc3)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2cc(-c3cccnc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2cc(-c3cccnc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 6-Pyridin-3-yl-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccncc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2ccc(-c3cccnc3)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2cc(-c3cccnc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cb2f0c9260ab4401a1e8545c8dcf5fe1 | COc1ccc(-c2ccc3c(c2)NC(=O)C3)cc1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>COc1ccc(-c2ccc3c(c2)NC(=O)C3=Cc2cc3cc(OCCN4CCCC4)ccc3[nH]2)cc1 | COC1=CC=C(C=C1)C1=CC=C2CC(NC2=C1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>COC1=CC=C(C=C1)C1=CC=C2C(C(NC2=C1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[NH:13][C:14](=[O:15])[CH2:16]3)[cH:35][cH:36]1.O=[CH:17][c:18]1[cH:19][c:20]2[cH:21][c:22]([O:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[nH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][... | COc1ccc(-c2ccc3c(c2)NC(=O)C3)cc1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | COc1ccc(-c2ccc3c(c2)NC(=O)C3=Cc2cc3cc(OCCN4CCCC4)ccc3[nH]2)cc1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 6-(4-Methoxy-phenyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | COc1ccc(-c2ccc3c(c2)NC(=O)C3)cc1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>COc1ccc(-c2ccc3c(c2)NC(=O)C3=Cc2cc3cc(OCCN4CCCC4)ccc3[nH]2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2cf45173a684aa69370eff88b705191 | COc1cccc(-c2ccc3c(c2)NC(=O)C3)c1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>COc1cccc(-c2ccc3c(c2)NC(=O)C3=Cc2cc3cc(OCCN4CCCC4)ccc3[nH]2)c1 | COC=1C=C(C=CC1)C1=CC=C2CC(NC2=C1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>COC=1C=C(C=CC1)C1=CC=C2C(C(NC2=C1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[NH:14][C:15](=[O:16])[CH2:17]3)[cH:36]1.O=[CH:18][c:19]1[cH:20][c:21]2[cH:22][c:23]([O:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[cH:32][cH:33][c:34]2[nH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][... | COc1cccc(-c2ccc3c(c2)NC(=O)C3)c1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | COc1cccc(-c2ccc3c(c2)NC(=O)C3=Cc2cc3cc(OCCN4CCCC4)ccc3[nH]2)c1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 6-(3-Methoxy-phenyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | COc1cccc(-c2ccc3c(c2)NC(=O)C3)c1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>COc1cccc(-c2ccc3c(c2)NC(=O)C3=Cc2cc3cc(OCCN4CCCC4)ccc3[nH]2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ca5c8715d5584f2e8a37aff103ced985 | COc1ccccc1-c1ccc2c(c1)NC(=O)C2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>COc1ccccc1-c1ccc2c(c1)NC(=O)C2=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | COC1=C(C=CC=C1)C1=CC=C2CC(NC2=C1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>COC1=C(C=CC=C1)C1=CC=C2C(C(NC2=C1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [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]2[c:13]([cH:14]1)[NH:15][C:16](=[O:17])[CH2:18]2.O=[CH:19][c:20]1[cH:21][c:22]2[cH:23][c:24]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:33][cH:34][c:35]2[nH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH... | COc1ccccc1-c1ccc2c(c1)NC(=O)C2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | COc1ccccc1-c1ccc2c(c1)NC(=O)C2=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 6-(2-Methoxy-phenyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2c(c1)CCN2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | COc1ccccc1-c1ccc2c(c1)NC(=O)C2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>COc1ccccc1-c1ccc2c(c1)NC(=O)C2=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1783069595d241b6a79d9f4b41a6ea47 | O=C1Cc2ccc(-c3ccc(F)cc3)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2cc(-c3ccc(F)cc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | FC1=CC=C(C=C1)C1=CC=C2CC(NC2=C1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>FC1=CC=C(C=C1)C1=CC=C2C(C(NC2=C1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]3)[cH:14][cH:15][c:16]2[CH2:17]1.O=[CH:18][c:19]1[cH:20][c:21]2[cH:22][c:23]([O:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[cH:32][cH:33][c:34]2[nH:35]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][c:10]([F:1... | O=C1Cc2ccc(-c3ccc(F)cc3)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2cc(-c3ccc(F)cc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2cc(-c3ccccc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 6-(4-Fluoro-phenyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2ccc(-c3ccc(F)cc3)cc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2cc(-c3ccc(F)cc3)ccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-19e07496845b43c59dc41f9f66a4c6b4 | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>NS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 | O=C1NC2=CC=C(C=C2C1)S(=O)(=O)N.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>O=C1NC2=CC=C(C=C2C1=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][C:30](=[O:31])[NH:32]2.O=[CH:12][c:13]1[cH:14][c:15]2[cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][cH:27][c:28]2[nH:29]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[CH:12][... | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | NS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 80 | [{"value": 80.0, "product": "O=C1NC2=CC=C(C=C2C1=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "O=C1NC2=CC=C(C=C2C1=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid amide (28 mg, 0.13 mmol), 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde (34 mg, 0.13 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 90° C. for 2 hours. The reaction was cooled at 0° C. for overnight. The precipitate was collected by vacuum ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.C1CC[NH]C1.c1ccc2c(c1)CCN2 | HO- | C(C)O | 90 | null | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>C(C)O>NS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-241186edc73a418b8d2223310676eef9 | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>>NS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCOCC4)ccc3[nH]1)C(=O)N2 | O=C1NC2=CC=C(C=C2C1)S(=O)(=O)N.N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=O.N1CCCCC1>>N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)S(=O)(=O)N)=O | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][C:31](=[O:32])[NH:33]2.O=[CH:12][c:13]1[cH:14][c:15]2[cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[cH:27][cH:28][c:29]2[nH:30]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[C... | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | NS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCOCC4)ccc3[nH]1)C(=O)N2 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 73.7 | [{"value": 62.0, "product": "N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)S(=O)(=O)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.7, "product": "N1(CCOCC1)CCOC=1C=C2C=C(NC2=CC1)C=C1C(NC2=CC=C(C=C12)S(=O)(=O)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid amide (27 mg, 0.12 mmol), 5-(2-morpholin-4-yl-ethoxy)-1H-indole-2-carbaldehyde (30 mg, 0.11 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 90° C. for 2 hours. The reaction was cooled at 0° C. for overnight. The precipitate was collected by vacuum f... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.C1COCC[NH]1.c1ccc2c(c1)CCN2 | HO- | C(C)O | 90 | null | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCOCC3)ccc2[nH]1>C(C)O>NS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCOCC4)ccc3[nH]1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-18a5845c22d848fda246f17d485f067b | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 | CNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>CNS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:31](=[O:32])[NH:33]2.O=[CH:13][c:14]1[cH:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[cH:27][cH:28][c:29]2[nH:30]1>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C... | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | CNS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.C1CC[NH]C1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d5e0e66c5314db79914bd9b95a53818 | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 | CN(S(=O)(=O)C=1C=C2CC(NC2=CC1)=O)C.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>CN(S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1)C | [CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][C:32](=[O:33])[NH:34]2.O=[CH:14][c:15]1[cH:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[cH:28][cH:29][c:30]2[nH:31]1>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2... | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid dimethylamide was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.C1CC[NH]C1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56759b568b2a4dffbb203a7ae0dc3451 | O=C1Cc2cc(S(=O)(=O)Nc3ccccc3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)Nc3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | C1(=CC=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>C1(=CC=CC=C1)NS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][c:19]2[CH2:20]1.O=[CH:21][c:22]1[cH:23][c:24]2[cH:25][c:26]([O:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)[cH:35][cH:36][c:37]2[nH:38]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([... | O=C1Cc2cc(S(=O)(=O)Nc3ccccc3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(S(=O)(=O)Nc3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(S(=O)(=O)Nc3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid phenylamide was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2cc(S(=O)(=O)Nc3ccccc3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)Nc3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aaab416f23394498be6144a2a3be3036 | O=C1Cc2cc(S(=O)(=O)Nc3cccnc3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)Nc3cccnc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | N1=CC(=CC=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>N1=CC(=CC=C1)NS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][c:12]3[cH:13][cH:14][cH:15][n:16][cH:17]3)[cH:18][c:19]2[CH2:20]1.O=[CH:21][c:22]1[cH:23][c:24]2[cH:25][c:26]([O:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)[cH:35][cH:36][c:37]2[nH:38]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([S... | O=C1Cc2cc(S(=O)(=O)Nc3cccnc3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(S(=O)(=O)Nc3cccnc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(S(=O)(=O)Nc3cccnc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid pyridin-3-ylamide was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccncc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2cc(S(=O)(=O)Nc3cccnc3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)Nc3cccnc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-912baefd6e374359b8bbe7b16e6030d9 | O=C1Cc2cc(S(=O)(=O)N3CCc4ccccc43)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)N3CCc4ccccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | N1(CCC2=CC=CC=C12)S(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>N1(CCC2=CC=CC=C12)S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[N:11]3[CH2:12][CH2:13][c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]43)[cH:20][c:21]2[CH2:22]1.O=[CH:23][c:24]1[cH:25][c:26]2[cH:27][c:28]([O:29][CH2:30][CH2:31][N:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)[cH:37][cH:38][c:39]2[nH:40]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH... | O=C1Cc2cc(S(=O)(=O)N3CCc4ccccc43)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(S(=O)(=O)N3CCc4ccccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(S(=O)(=O)N3CCc4ccccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 5-(2,3-Dihydro-indole-1-sulfonyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2c(c1)CC[NH]2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2cc(S(=O)(=O)N3CCc4ccccc43)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)N3CCc4ccccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f1249bb3463e43fc971683f1618fa3f1 | O=C1Cc2cc(S(=O)(=O)Nc3cccc(Cl)c3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)Nc3cccc(Cl)c3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | ClC=1C=C(C=CC1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>ClC=1C=C(C=CC1)NS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]3)[cH:19][c:20]2[CH2:21]1.O=[CH:22][c:23]1[cH:24][c:25]2[cH:26][c:27]([O:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)[cH:36][cH:37][c:38]2[nH:39]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6... | O=C1Cc2cc(S(=O)(=O)Nc3cccc(Cl)c3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(S(=O)(=O)Nc3cccc(Cl)c3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(S(=O)(=O)Nc3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chloro-phenyl)-amide was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2cc(S(=O)(=O)Nc3cccc(Cl)c3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)Nc3cccc(Cl)c3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5185e09d5e6d4195a51e1e81a27f719f | CN(c1cccc(Cl)c1)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>CN(c1cccc(Cl)c1)S(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 | ClC=1C=C(C=CC1)N(S(=O)(=O)C=1C=C2CC(NC2=CC1)=O)C.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>ClC=1C=C(C=CC1)N(S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1)C | [CH3:1][N:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([Cl:8])[cH:9]1)[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]2[c:17]([cH:18]1)[CH2:19][C:38](=[O:39])[NH:40]2.O=[CH:20][c:21]1[cH:22][c:23]2[cH:24][c:25]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:34][cH:35][c:36]2[nH:37]1>>[CH3:1][N:2]([c:3]1[cH:4... | CN(c1cccc(Cl)c1)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | CN(c1cccc(Cl)c1)S(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(S(=O)(=O)Nc3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chloro-phenyl)-methyl-amide was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN(c1cccc(Cl)c1)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>CN(c1cccc(Cl)c1)S(=O)(=O)c1ccc2c(c1)C(=Cc1cc3cc(OCCN4CCCC4)ccc3[nH]1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-761d67e44fe44f0eb630ad7a82a65292 | O=C1Cc2cc(S(=O)(=O)Nc3ccc(Cl)cc3F)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)Nc3ccc(Cl)cc3F)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | ClC1=CC(=C(C=C1)NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O)F.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>ClC1=CC(=C(C=C1)NS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1)F | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]3[F:19])[cH:20][c:21]2[CH2:22]1.O=[CH:23][c:24]1[cH:25][c:26]2[cH:27][c:28]([O:29][CH2:30][CH2:31][N:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)[cH:37][cH:38][c:39]2[nH:40]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5]... | O=C1Cc2cc(S(=O)(=O)Nc3ccc(Cl)cc3F)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(S(=O)(=O)Nc3ccc(Cl)cc3F)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(S(=O)(=O)Nc3ccccc3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid (4-chloro-2-fluoro-phenyl)-amide was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2cc(S(=O)(=O)Nc3ccc(Cl)cc3F)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)Nc3ccc(Cl)cc3F)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56ca174cccc0454db76b75734fbc8ed9 | O=C1Cc2cc(S(=O)(=O)N3CCCc4ccccc43)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)N3CCCc4ccccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | N1(CCCC2=CC=CC=C12)S(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>N1(CCCC2=CC=CC=C12)S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[N:11]3[CH2:12][CH2:13][CH2:14][c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]43)[cH:21][c:22]2[CH2:23]1.O=[CH:24][c:25]1[cH:26][c:27]2[cH:28][c:29]([O:30][CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:38][cH:39][c:40]2[nH:41]1>>[O:1]=[C:2]1[NH:3][... | O=C1Cc2cc(S(=O)(=O)N3CCCc4ccccc43)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(S(=O)(=O)N3CCCc4ccccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(S(=O)(=O)N3CCCc4ccccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 5-(3,4-Dihydro-2H-quinoline-1-sulfonyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2c(c1)CCC[NH]2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2cc(S(=O)(=O)N3CCCc4ccccc43)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)N3CCCc4ccccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b57b2ba515740d182c9f72c3c926337 | O=C1Cc2cc(S(=O)(=O)N3CCc4ccccc4C3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)N3CCc4ccccc4C3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | C1N(CCC2=CC=CC=C12)S(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>C1N(CCC2=CC=CC=C12)S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[N:11]3[CH2:12][CH2:13][c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]4[CH2:20]3)[cH:21][c:22]2[CH2:23]1.O=[CH:24][c:25]1[cH:26][c:27]2[cH:28][c:29]([O:30][CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:38][cH:39][c:40]2[nH:41]1>>[O:1]=[C:2]1[NH:3][... | O=C1Cc2cc(S(=O)(=O)N3CCc4ccccc4C3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(S(=O)(=O)N3CCc4ccccc4C3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(S(=O)(=O)N3CCc4ccccc4C3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 5-(3,4-Dihydro-1H-isoquinoline-2-sulfonyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2c(c1)CC[NH]C2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2cc(S(=O)(=O)N3CCc4ccccc4C3)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)N3CCc4ccccc4C3)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11d7d2d1664f48f6a210a9fc7908bcb9 | O=C1Cc2cc(S(=O)(=O)N3CCc4cc(Br)ccc43)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)N3CCc4cc(Br)ccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | BrC=1C=C2CCN(C2=CC1)S(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1(CCCC1)CCOC=1C=C2C=C(NC2=CC1)C=O>>BrC=1C=C2CCN(C2=CC1)S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=C(C=C2C1)OCCN1CCCC1 | [O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[N:11]3[CH2:12][CH2:13][c:14]4[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]43)[cH:21][c:22]2[CH2:23]1.O=[CH:24][c:25]1[cH:26][c:27]2[cH:28][c:29]([O:30][CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)[cH:38][cH:39][c:40]2[nH:41]1>>[O:1]=[C:2]1[NH:3][... | O=C1Cc2cc(S(=O)(=O)N3CCc4cc(Br)ccc43)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=C1Nc2ccc(S(=O)(=O)N3CCc4cc(Br)ccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccc(S(=O)(=O)N3CCc4ccccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 5-(5-Bromo-2,3-dihydro-indole-1-sulfonyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2.c1ccc2c(c1)CC[NH]2.c1ccc2[nH]ccc2c1.C1CC[NH]C1 | HO- | null | null | null | O=C1Cc2cc(S(=O)(=O)N3CCc4cc(Br)ccc43)ccc2N1.O=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1>>O=C1Nc2ccc(S(=O)(=O)N3CCc4cc(Br)ccc43)cc2C1=Cc1cc2cc(OCCN3CCCC3)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eefb09cc57f1464a80b035879f843490 | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1c[nH]c2ccccc12>>NS(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 | NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1C=C(C2=CC=CC=C12)C=O>>N1C=C(C2=CC=CC=C12)C=C1C(NC2=CC=C(C=C12)S(=O)(=O)N)=O | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][C:22](=[O:23])[NH:24]2.O=[CH:12][c:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[CH:12][c:13]1[cH:14][nH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]13... | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1c[nH]c2ccccc12 | NS(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1c[nH]c2ccccc12 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[O;D1;H0:7]=[C:8]1-[#7:9]-[c:10]:[c:11](:[c:12])-[CH2;D2;+0:13]-1>>[O;D1;H0:7]=[C:8]1-[#7:9]-[c:10]:[c:11](:[c:12])-[C;H0;D3;+0:13]-1=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1 | null | [] | null | null | null | null | 5-Aminosulfonyl-2-oxindole was condensed with indole-3-carboxaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1c[nH]c2ccccc12>>NS(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7c01d6713a334e4e94297e04754df548 | Cc1[nH]c2ccccc2c1C=O.NS(=O)(=O)c1ccc2c(c1)CC(=O)N2>>Cc1[nH]c2ccccc2c1C=C1C(=O)Nc2ccc(S(N)(=O)=O)cc21 | NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.CC=1NC2=CC=CC=C2C1C=O>>CC=1NC2=CC=CC=C2C1C=C1C(NC2=CC=C(C=C12)S(=O)(=O)N)=O | O=[CH:11][c:10]1[c:2]([CH3:1])[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]21.[CH2:12]1[C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][c:19]([S:20]([NH2:21])(=[O:22])=[O:23])[cH:24][c:25]21>>[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[C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][c:19]([S:20]([NH... | Cc1[nH]c2ccccc2c1C=O.NS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | Cc1[nH]c2ccccc2c1C=C1C(=O)Nc2ccc(S(N)(=O)=O)cc21 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1c[nH]c2ccccc12 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].[O;D1;H0:8]=[C:9]1-[#7:10]-[c:11]:[c:12](:[c:13])-[CH2;D2;+0:14]-1>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:1-[CH;D2;+0:1]=[C;H0;D3;+0:14]1-[C:9](=[O;D1;H0:8])-[#7:10]-[c:11]:[c:12]-1:[c:13] | null | [] | null | null | null | null | 5-Aminosulfonyl-2-oxindole was condensed with 2-methylindole-3-carboxaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | Cc1[nH]c2ccccc2c1C=O.NS(=O)(=O)c1ccc2c(c1)CC(=O)N2>>Cc1[nH]c2ccccc2c1C=C1C(=O)Nc2ccc(S(N)(=O)=O)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f0b61d8e33346a3b4c2b876a8ce1200 | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1ccc2[nH]ccc2c1>>NS(=O)(=O)c1ccc2c(c1)C(=Cc1ccc3[nH]ccc3c1)C(=O)N2 | NS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1C=CC2=CC(=CC=C12)C=O>>N1C=CC2=CC(=CC=C12)C=C1C(NC2=CC=C(C=C12)S(=O)(=O)N)=O | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][C:22](=[O:23])[NH:24]2.O=[CH:12][c:13]1[cH:14][cH:15][c:16]2[nH:17][cH:18][cH:19][c:20]2[cH:21]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[CH:12][c:13]1[cH:14][cH:15][c:16]3[nH:17][cH:18][cH:19][c:20]3[cH:21]1... | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1ccc2[nH]ccc2c1 | NS(=O)(=O)c1ccc2c(c1)C(=Cc1ccc3[nH]ccc3c1)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1ccc2[nH]ccc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:11]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 5-Aminosulfonyl-2-oxindole was condensed with indole-5-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1ccc2[nH]ccc2c1>>NS(=O)(=O)c1ccc2c(c1)C(=Cc1ccc3[nH]ccc3c1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cff604755d1e48cb9b30135a19538de1 | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1c[nH]c2ccccc12>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 | CNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1C=C(C2=CC=CC=C12)C=O>>CNS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC1=CNC2=CC=CC=C12 | [CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:23](=[O:24])[NH:25]2.O=[CH:13][c:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[CH:13][c:14]1[cH:15][nH:16][c:17]3[cH:18][cH:19][cH:20][... | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1c[nH]c2ccccc12 | CNS(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1c[nH]c2ccccc12 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[O;D1;H0:7]=[C:8]1-[#7:9]-[c:10]:[c:11](:[c:12])-[CH2;D2;+0:13]-1>>[O;D1;H0:7]=[C:8]1-[#7:9]-[c:10]:[c:11](:[c:12])-[C;H0;D3;+0:13]-1=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1 | null | [] | null | null | null | null | 5-Methylaminosulfonyl-2-oxindole was condensed with indole-3-carboxaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1c[nH]c2ccccc12>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d439e4333f1249a6914b47767a3eae78 | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.Cc1[nH]c2ccccc2c1C=O>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1c(C)[nH]c3ccccc13)C(=O)N2 | CNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.CC=1NC2=CC=CC=C2C1C=O>>CNS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC1=C(NC2=CC=CC=C12)C | [CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:24](=[O:25])[NH:26]2.O=[CH:13][c:14]1[c:15]([CH3:16])[nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[CH:13][c:14]1[c:15]([CH3:16])[nH:17][c:18]3[cH:... | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.Cc1[nH]c2ccccc2c1C=O | CNS(=O)(=O)c1ccc2c(c1)C(=Cc1c(C)[nH]c3ccccc13)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1c[nH]c2ccccc12 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].[O;D1;H0:8]=[C:9]1-[#7:10]-[c:11]:[c:12](:[c:13])-[CH2;D2;+0:14]-1>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:1-[CH;D2;+0:1]=[C;H0;D3;+0:14]1-[C:9](=[O;D1;H0:8])-[#7:10]-[c:11]:[c:12]-1:[c:13] | null | [] | null | null | null | null | 5-Methylaminosulfonyl-2-oxindole was condensed with 2-methylindole-3-carboxaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.Cc1[nH]c2ccccc2c1C=O>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1c(C)[nH]c3ccccc13)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-356051b0590f416ba6c40dbefbaae9e2 | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1ccc2[nH]ccc2c1>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1ccc3[nH]ccc3c1)C(=O)N2 | CNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1C=CC2=CC(=CC=C12)C=O>>CNS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1C=C2C=CNC2=CC1 | [CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:23](=[O:24])[NH:25]2.O=[CH:13][c:14]1[cH:15][cH:16][c:17]2[nH:18][cH:19][cH:20][c:21]2[cH:22]1>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[CH:13][c:14]1[cH:15][cH:16][c:17]3[nH:18][cH:19][cH:20][... | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1ccc2[nH]ccc2c1 | CNS(=O)(=O)c1ccc2c(c1)C(=Cc1ccc3[nH]ccc3c1)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1ccc2[nH]ccc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:11]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 5-Methylaminosulfonyl-2-oxindole was condensed with indole-5-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1ccc2[nH]ccc2c1>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1ccc3[nH]ccc3c1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0424d0f50cd444249f992a12375867be | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2ccccc2[nH]1>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3ccccc3[nH]1)C(=O)N2 | CNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1C(=CC2=CC=CC=C12)C=O>>CNS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=CC=C2C1 | [CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:23](=[O:24])[NH:25]2.O=[CH:13][c:14]1[cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[nH:22]1>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[CH:13][c:14]1[cH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][... | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2ccccc2[nH]1 | CNS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3ccccc3[nH]1)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 5-Methylaminosulfonyl-2-oxindole was condensed with indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2ccccc2[nH]1>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3ccccc3[nH]1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1869efa9087c449794a4fd37192139b2 | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1c[nH]c2ccccc12>>CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 | CN(S(=O)(=O)C=1C=C2CC(NC2=CC1)=O)C.N1C=C(C2=CC=CC=C12)C=O>>CN(S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC1=CNC2=CC=CC=C12)C | [CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][C:24](=[O:25])[NH:26]2.O=[CH:14][c:15]1[cH:16][nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[C:13](=[CH:14][c:15]1[cH:16][nH:17][c:18]3[cH:... | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1c[nH]c2ccccc12 | CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1c[nH]c2ccccc12 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[O;D1;H0:7]=[C:8]1-[#7:9]-[c:10]:[c:11](:[c:12])-[CH2;D2;+0:13]-1>>[O;D1;H0:7]=[C:8]1-[#7:9]-[c:10]:[c:11](:[c:12])-[C;H0;D3;+0:13]-1=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]:1 | null | [] | null | null | null | null | 5-Dimethylaminosulfonyl-2-oxindole was condensed with indole-3-carboxaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1c[nH]c2ccccc12>>CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea6d4862d41645c8b83f546ebd6d67df | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.Cc1[nH]c2ccccc2c1C=O>>Cc1[nH]c2ccccc2c1C=C1C(=O)Nc2ccc(S(=O)(=O)N(C)C)cc21 | CN(S(=O)(=O)C=1C=C2CC(NC2=CC1)=O)C.CC=1NC2=CC=CC=C2C1C=O>>CN(S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC1=C(NC2=CC=CC=C12)C)C | [CH2:12]1[C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][c:19]([S:20](=[O:21])(=[O:22])[N:23]([CH3:24])[CH3:25])[cH:26][c:27]21.O=[CH:11][c:10]1[c:2]([CH3:1])[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]21>>[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[C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][... | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.Cc1[nH]c2ccccc2c1C=O | Cc1[nH]c2ccccc2c1C=C1C(=O)Nc2ccc(S(=O)(=O)N(C)C)cc21 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1c[nH]c2ccccc12 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].[O;D1;H0:8]=[C:9]1-[#7:10]-[c:11]:[c:12](:[c:13])-[CH2;D2;+0:14]-1>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:1-[CH;D2;+0:1]=[C;H0;D3;+0:14]1-[C:9](=[O;D1;H0:8])-[#7:10]-[c:11]:[c:12]-1:[c:13] | null | [] | null | null | null | null | 5-Dimethylaminosulfonyl-2-oxindole was condensed with 2-methylindole-3-carboxaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.Cc1[nH]c2ccccc2c1C=O>>Cc1[nH]c2ccccc2c1C=C1C(=O)Nc2ccc(S(=O)(=O)N(C)C)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-81a0545aa45441b38df6ed0bf465500f | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1ccc2[nH]ccc2c1>>CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1ccc3[nH]ccc3c1)C(=O)N2 | CN(S(=O)(=O)C=1C=C2CC(NC2=CC1)=O)C.N1C=CC2=CC(=CC=C12)C=O>>CN(S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1C=C2C=CNC2=CC1)C | [CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][C:24](=[O:25])[NH:26]2.O=[CH:14][c:15]1[cH:16][cH:17][c:18]2[nH:19][cH:20][cH:21][c:22]2[cH:23]1>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[C:13](=[CH:14][c:15]1[cH:16][cH:17][c:18]3[nH:... | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1ccc2[nH]ccc2c1 | CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1ccc3[nH]ccc3c1)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1ccc2[nH]ccc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:11]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 5-Dimethylaminosulfonyl-2-oxindole was condensed with indole-5-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1ccc2[nH]ccc2c1>>CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1ccc3[nH]ccc3c1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a92cac139a54072a0d72a02ede865c4 | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2ccccc2[nH]1>>CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1cc3ccccc3[nH]1)C(=O)N2 | CN(S(=O)(=O)C=1C=C2CC(NC2=CC1)=O)C.N1C(=CC2=CC=CC=C12)C=O>>CN(S(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=CC=C2C1)C | [CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][C:24](=[O:25])[NH:26]2.O=[CH:14][c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[nH:23]1>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[C:13](=[CH:14][c:15]1[cH:16][c:17]3[cH:18][cH:... | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2ccccc2[nH]1 | CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1cc3ccccc3[nH]1)C(=O)N2 | null | null | null | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 5-Dimethylaminosulfonyl-2-oxindole was condensed with indole-2-carbaldehyde to give the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CN(C)S(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1cc2ccccc2[nH]1>>CN(C)S(=O)(=O)c1ccc2c(c1)C(=Cc1cc3ccccc3[nH]1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0c8ea1a30ab49e8b83c7c4cd4c8cbec | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.COc1cccc2[nH]c(C=O)cc12>>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3c(OC)cccc3[nH]1)C(=O)N2 | CNS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.COC1=C2C=C(NC2=CC=C1)C=O.N1CCCCC1>>CNS(=O)(=O)C=1C=C2C(C(NC2=CC1)=O)=CC=1NC2=CC=CC(=C2C1)OC | [CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:25](=[O:26])[NH:27]2.O=[CH:13][c:14]1[cH:15][c:16]2[c:17]([O:18][CH3:19])[cH:20][cH:21][cH:22][c:23]2[nH:24]1>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[CH:13][c:14]1[cH:15][c:16]3[c:17]([O:18][... | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.COc1cccc2[nH]c(C=O)cc12 | CNS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3c(OC)cccc3[nH]1)C(=O)N2 | null | null | C(C)O | C-C Coupling | Aldol condensation | d4da47c26a7e98de652f649c74b8a3edf371eb0fe9d1976c609c3297e2558278 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Nc2ccccc2C1=Cc1cc2ccccc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | 5 | DAY | A mixture of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide (194 mg, 0.86 mmol), 4-methoxy-1H-indole-2-carbaldehyde (150 mg, 0.86 mmol) and piperidine (36 mg, 0.43 mmol) in ethanol (0.2 M) was stirred at room temperature for a total of 5 days. The reaction was concentrated to ¼ of its volume and the precipitat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CCN2 | HO- | C(C)O | null | 120 | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2.COc1cccc2[nH]c(C=O)cc12>C(C)O>CNS(=O)(=O)c1ccc2c(c1)C(=Cc1cc3c(OC)cccc3[nH]1)C(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ba78f745c98646a2bec87c6fbb926902 | C1CCNC1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>>O=C1Cc2cc(S(=O)(=O)N3CCCC3)ccc2N1 | Cl.ClS(=O)(=O)C=1C=C2CC(NC2=CC1)=O.N1CCCC1.N1=CC=CC=C1>>N1(CCCC1)S(=O)(=O)C=1C=C2CC(NC2=CC1)=O | [NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1.Cl[S:7]([c:6]1[cH:5][c:4]2[c:17]([cH:16][cH:15]1)[NH:18][C:2](=[O:1])[CH2:3]2)(=[O:8])=[O:9]>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:15][cH:16][c:17]2[NH:18]1 | C1CCNC1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1 | O=C1Cc2cc(S(=O)(=O)N3CCCC3)ccc2N1 | null | null | ClCCl.C(C)(=O)OCC | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | f3c6fed690e733503a3f0544b78d62f7ee997af455c39a6e6ee11bc2902547ad | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C1Cc2cc(S(=O)(=O)N3CCCC3)ccc2N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1)-[c:4](:[c:5]):[c:6] | 27 | [{"value": 27.0, "product": "N1(CCCC1)S(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.2, "product": "N1(CCCC1)S(=O)(=O)C=1C=C2CC(NC2=CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A suspension of 5-chlorosulfonyl-2-oxindole (1.62 g, 7 mmol), pyrrolidine (0.701 mL, 8.4 mmol) and pyridine (1 mL) in dichloromethane (20 mL) was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and made acidic with 1 N hydrochloric acid (16 mL). The organic layer wa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccc2c(c1)CCN2.C1CC[NH]C1 | HCl | ClCCl.C(C)(=O)OCC | null | 4 | C1CCNC1.O=C1Cc2cc(S(=O)(=O)Cl)ccc2N1>ClCCl.C(C)(=O)OCC>O=C1Cc2cc(S(=O)(=O)N3CCCC3)ccc2N1 |
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