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【结 构 式】 
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【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% |
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 |