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【结 构 式】

【分子编号】41235

【品名】6-methoxy-1,3-dihydro-2H-indol-2-one

【CA登记号】

【 分 子 式 】C9H9NO2

【 分 子 量 】163.176

【元素组成】C 66.25% H 5.56% N 8.58% O 19.61%

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:(I)

The Friedel Crafts condensation of 6-methoxyindolin-2-one (I) with acetyl chloride and AlCl3 gives the 5-acetyl-6-methoxyindolin-2-one (II), which is treated with hydroxylamine and acetic anhydride to yield the O-acetyloxime (III). The cyclization of (III) affords the 3-methyl-6,7-dihydro-5H-isoxazolo[4,5-f]indol-6-one (IV), which is condensed with 4-(iodomethyl)piperidine-1-carboxylic acid tert-butyl ester (V) to provide the adduct (VI). Finally this compound is deprotected with TFA and benzylated with benzyl bromide (VII) to furnish the target compound.

1 Maggi, A.; Brufani, M.; Lappa, S.; Filocamo, L.; New acetylcholinesterease inhibitors. Drugs Fut 1997, 22, 4, 397.
2 Villalobos, A.; et al.; 5, 7-Dihydro-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-6H-pyrrolo[3,2-f]-1,2-benzisoxaxol-6-one: A potent and centrally-selective inhibitor of acetylcholinesterase with an improved margin of safety. J Med Chem 1995, 38, 15, 2802.
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) 41235 6-methoxy-1,3-dihydro-2H-indol-2-one C9H9NO2 详情 详情
(II) 41236 5-acetyl-6-hydroxy-1,3-dihydro-2H-indol-2-one C10H9NO3 详情 详情
(III) 41237 5-ethanimidoyl-6-hydroxy-1,3-dihydro-2H-indol-2-one C12H12N2O4 详情 详情
(IV) 41238 3-methyl-5,7-dihydro-6H-isoxazolo[4,5-f]indol-6-one C10H8N2O2 详情 详情
(V) 41239 tert-butyl 4-(iodomethyl)-1-piperidinecarboxylate C11H20INO2 详情 详情
(VI) 41240 tert-butyl 4-[2-(6-oxo-6,7-dihydro-5H-isoxazolo[4,5-f]indol-3-yl)ethyl]-1-piperidinecarboxylate C21H27N3O4 详情 详情
(VII) 12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
Extended Information