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【结 构 式】

【分子编号】40474

【品名】phenyl 5-chloro-2-[(phenoxycarbonyl)oxy]-1H-indole-1-carboxylate

【CA登记号】

【 分 子 式 】C22H14ClNO5

【 分 子 量 】407.8096

【元素组成】C 64.8% H 3.46% Cl 8.69% N 3.43% O 19.62%

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:(II)

A new synthesis of tenidap has been developed: The reaction of 5-chloroindolin-2-one (I) with phenyl chloroformate and Et3N in THF gives 5-chloro-2-(phenoxycarbonyloxy)indole-1-carboxylic acid phenyl ester (II), which is treated with ammonium carbonate in DMF at 5 C yielding 5-chloro-2-oxoindoline-1-carboxylic acid phenyl ester (III). Compound (III) is acylated with 2-thienylcarbonyl chloride (IV) and DMAP in DMF and then acidified with conc. HCl affording 5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-2-oxoindoline-1-carboxylic acid phenyl ester (V), which is finally treated with ammonium carbonate in DMF at 75-80 C for 5 h and acidified with conc. HCl.

1 Siming, G.; Porcs-Makkay, M.; New practical synthesis of tenidap. Org Process Res Dev 2000, 4, 1, 10.
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) 14100 5-Chlorooxindole; 5-Chloro-1,3-dihydro-2H-indol-2-one 17630-75-0 C8H6ClNO 详情 详情
(II) 40474 phenyl 5-chloro-2-[(phenoxycarbonyl)oxy]-1H-indole-1-carboxylate C22H14ClNO5 详情 详情
(III) 40475 phenyl 5-chloro-2-oxo-1-indolinecarboxylate C15H10ClNO3 详情 详情
(IV) 14103 2-Thiophenecarbonyl chloride 5271-67-0 C5H3ClOS 详情 详情
(V) 40476 phenyl 5-chloro-3-[(Z)-hydroxy(2-thienyl)methylidene]-2-oxo-1H-indole-1(2H)-carboxylate C20H12ClNO4S 详情 详情
Extended Information