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【结 构 式】

【分子编号】65866

【品名】2-bromo-8-fluoro-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one

【CA登记号】 

【 分 子 式 】C11H8BrFN2O

【 分 子 量 】283.0998032

【元素组成】C 46.67% H 2.85% Br 28.22% F 6.71% N 9.9% O 5.65%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

Reductive cyclization of 6-fluoro-3-(2-nitroethyl)-1H-indole-4-carboxylic acid methyl ester (I) by means of Zn and HCl in methanol/water gives 8-fluoro-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one (II), which is brominated by means of Pyr/HBr/Br2 in THF/dichloromethane to afford the 2-bromo derivative (III). Condensation of the brominated compound (III) with 4-formylphenylboronic acid (IV) by means of Pd(PPh3)4 and Na2CO3 in refluxing H2O/ethanol/toluene provides 8-fluoro-2-(4-formylphenyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one (V), which is finally reductocondensed with methylamine (VI) by means of NaBH4 (1). Scheme 1.

1 Webber, S.E., Thoresen, L.H., Tikhe, H., Canan-Koch, S.S. (Agouron Pharmaceuticals, Inc.; Cancer Research UK). Tricyclic inhibitors of poly(ADP-ribose) polymerases. CA 2360003, EP 1140936, JP 2002534523, US 6495541, WO 2000042040.
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) 65864 6-fluoro-3-(2-nitroethyl)-1H-indole-4-carboxylic acid methyl ester   C12H11FN2O4 详情 详情
(II) 65865 8-fluoro-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one   C11H9FN2O 详情 详情
(III) 65866 2-bromo-8-fluoro-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one   C11H8BrFN2O 详情 详情
(IV) 61564 4-Formylphenylboronic acid; 4-Formylbenzeneboronic acid; 4-Boronobenzaldehyde; Benzaldehyde-4-boronic acid; 4-Formylphenylboronic acid 87199-17-5 C7H7BO3 详情 详情
(V) 65867 8-fluoro-2-(4-formylphenyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one   C18H13FN2O2 详情 详情
(VI) 11021 Methanamine; Methylamine 74-89-5 CH5N 详情 详情
Extended Information