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【结 构 式】 
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【分子编号】39754 【品名】3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propionic acid 【CA登记号】 |
【 分 子 式 】C10H13NO3 【 分 子 量 】195.21816 【元素组成】C 61.53% H 6.71% N 7.17% O 24.59% |
合成路线1
该中间体在本合成路线中的序号：(IV)Basic hydrolysis of the known 2,4-dimethyl-5-ethoxycarbonyl-3-(2-ethoxycarbonyl ethyl)pyrrole (I) and subsequent decarboxylation of the resulting diacid (II) in the presence of HCl furnished 2,4-dimethyl-3-pyrrolepropionic acid (III). Vilsmeier formylation of (III) employing dimethylformamide and POCl3 produced aldehyde (IV). The title compound was then obtained by condensation of aldehyde (IV) with oxindole (V) in the presence of pyrrolidine, followed by acid treatment of the intermediate (VI). Alternatively, direct condensation of aldehyde (IV) with oxindole (V) in the presence of NaOH gave rise to the title compound.
| 【1】 Tang, P.C.; Sun, L.; McMahon, G. (Sugen, Inc.); Pyrrole substd. 2-indolinone protein kinase inhibitors. WO 9961422 . |
| 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) | 39751 | ethyl 4-(3-ethoxy-3-oxopropyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate | C14H21NO4 | 详情 | 详情 | |
| (II) | 39752 | 4-(2-carboxyethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid | C10H13NO4 | 详情 | 详情 | |
| (III) | 39753 | 3-(2,4-dimethyl-1H-pyrrol-3-yl)propionic acid | C9H13NO2 | 详情 | 详情 | |
| (IV) | 39754 | 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propionic acid | C10H13NO3 | 详情 | 详情 | |
| (V) | 18699 | 1,3-dihydro-2H-indol-2-one | 59-48-3 | C8H7NO | 详情 | 详情 |
| (VI) | 39755 | 3-[2,4-dimethyl-5-[(2-oxo-2,3-dihydro-1H-indol-3-yl)(1-pyrrolidinyl)methyl]-1H-pyrrol-3-yl]propionic acid | C22H27N3O3 | 详情 | 详情 |