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【结 构 式】 
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【分子编号】13004 【品名】4-(5-Methoxy-1H-indol-3-yl)-1-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]-1-butanone 【CA登记号】 |
【 分 子 式 】C24H26N2O2 【 分 子 量 】374.48272 【元素组成】C 76.98% H 7% N 7.48% O 8.54% |
合成路线1
该中间体在本合成路线中的序号：(VI)By demethylation of 5-methoxy-3-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-1H-indole (I) with diisobutylaluminum hydride (DBH) in hot toluene. The methylated compound (I) can be obtained by two similar ways: a) By condensation of 3-(4-chlorobutyl)-5-methoxy-1H-indole (II), or 3-(4-bromobutyl)-5-methoxy-1H-indole (III) with 4-phenyl-1,2,3,6-tetrahydropyridine (IV) in acetonitrile at room temperature. b) By condensation of 4-(3-indolyl)butyric acid (V) with 4-phenyl-1,2,3,6-tetrahydropyridine (IV) by means of carbonyldiimdazole (CDI) in THF yielding 1-[4-(3-indolyl)butyryl]-4-phenyl-1,2,3,6-tetrahydropyridine (VI), followed by reduction of the carbonyl group of (VI) with LiAlH4 in THF.
| 【1】 Robinson, C.; Castaner, J.; Roxindole Mesylate. Drugs Fut 1995, 20, 12, 1228. |
| 【2】 Hausberg, H.-H.; Bottcher, H.; Seyfried, C.; Bergmann, R. (Merck Patent GmbH); Use of hydroxyindole derivs. for the preparation of an antihypertensive agent. DE 3419935; EP 0166183; JP 1985258117; US 4711893 . |
| 【3】 Hausberg, H.-H.; Koppe, V.; Poetsch, E.; Saiko, O.; Seyfried, C. (Merck Patent GmbH); Indolalkylamines, pharmaceutical compsns. containing them and process for their preparation. EP 0007399 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 12999 | 5-Methoxy-3-[4-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]butyl]-1H-indole; Methyl 3-[4-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]butyl]-1H-indol-5-yl ether | C24H28N2O | 详情 | 详情 | |
| (II) | 13000 | 3-(4-Chlorobutyl)-1H-indol-5-yl methyl ether; 3-(4-Chlorobutyl)-5-methoxy-1H-indole | C13H16ClNO | 详情 | 详情 | |
| (III) | 13001 | 3-(4-Bromobutyl)-1H-indol-5-yl methyl ether; 3-(4-Bromobutyl)-5-methoxy-1H-indole | C13H16BrNO | 详情 | 详情 | |
| (IV) | 13002 | 4-Phenyl-1,2,3,6-tetrahydropyridine; 1,2,3,6-Tetrahydro-4-phenyl-pyridine | 10338-69-9 | C11H13N | 详情 | 详情 |
| (V) | 13003 | 4-(5-Methoxy-1H-indol-3-yl)butyric acid | C13H15NO3 | 详情 | 详情 | |
| (VI) | 13004 | 4-(5-Methoxy-1H-indol-3-yl)-1-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]-1-butanone | C24H26N2O2 | 详情 | 详情 |