• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】12999

【品名】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

【CA登记号】

【 分 子 式 】C24H28N2O

【 分 子 量 】360.4992

【元素组成】C 79.96% H 7.83% N 7.77% O 4.44%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

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

合成路线2

该中间体在本合成路线中的序号:(VI)

A new synthesis of roxindole has been described: The condensation of 5-methoxyindole (I) with succinic anhydride (II) by means of methylmagnesium bromide in hot anisole gives the 4-oxobutyric acid derivative (III), which is condensed with the 4-phenyltetrahydropyridine (IV) by means of EDC and DIPEA in DMF yielding the butanedione (V). The reduction of (V) with LiAlH4 in refluxing THF affords intermediate (VI), which is finally demethylated with DIBAH in refluxing toluene.

1 Lange, J.H.M.; et al.; A straightforward synthetic approach for roxindole. Bioorg Med Chem Lett 1999, 9, 7, 1055.
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) 25902 1H-Indol-5-yl methyl ether; 5-Methoxy-1H-indole; 5-Methoxyindole 1006-94-6 C9H9NO 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(III) 30614 4-(5-methoxy-1H-indol-3-yl)-4-oxobutyric acid C13H13NO4 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) 30615 1-(5-methoxy-1H-indol-3-yl)-4-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]-1,4-butanedione C24H24N2O3 详情 详情
(VI) 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
Extended Information