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【结 构 式】 
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【分子编号】60383 【品名】5-formyl-2,4-dimethyl-N-[2-(1-pyrrolidinyl)ethyl]-1H-pyrrole-3-carboxamide 【CA登记号】 |
【 分 子 式 】C14H21N3O2 【 分 子 量 】263.33976 【元素组成】C 63.85% H 8.04% N 15.96% O 12.15% |
合成路线1
该中间体在本合成路线中的序号：(V)Vilsmeier formylation of ethyl 2,4-dimethylindole-3-carboxylate (I) by means of POCl3 and DMF leads to aldehyde (II). Subsequent ester group hydrolysis in (II) under alkaline conditions furnishes acid (III), which is then coupled to N-(2-aminoethyl)pyrrolidine (IV) employing EDC/HOBt to afford the corresponding amide (V). Chemoselective reduction of the 3-carbonyl group of 5-fluoroisatin (VI) upon heating with hydrazine hydrate gives rise to 5-fluorooxindole (VII). Finally, condensation of (VII) with aldehyde (V) under Knoevenagel conditions provides the title compound
| 【1】 Wei, C.C.; Miller, T.; Tang, P.C.; Nematalla, A.S.; Li, X.; Liang, C.; Shirazian, S.; Su, L.; Vojkovsky, T. (Sugen, Inc.); Pyrrole substd. 2-indolinone protein kinase inhibitors. EP 1255752; US 2002156292; US 6573293; WO 0160814 . |
| 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) | 60380 | ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate | 2199-51-1 | C9H13NO2 | 详情 | 详情 |
| (II) | 60381 | ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate | 2199-59-9 | C10H13NO3 | 详情 | 详情 |
| (III) | 60382 | 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid | 253870-02-9 | C8H9NO3 | 详情 | 详情 |
| (IV) | 18161 | 2-(1-pyrrolidinyl)ethylamine; 2-(1-pyrrolidinyl)-1-ethanamine; 1-Pyrrolidineethanamine | 7154-73-6 | C6H14N2 | 详情 | 详情 |
| (V) | 60383 | 5-formyl-2,4-dimethyl-N-[2-(1-pyrrolidinyl)ethyl]-1H-pyrrole-3-carboxamide | C14H21N3O2 | 详情 | 详情 | |
| (VI) | 21552 | 5-fluoro-1H-indole-2,3-dione | 443-69-6 | C8H4FNO2 | 详情 | 详情 |
| (VII) | 60384 | 5-fluoro-1,3-dihydro-2H-indol-2-one | 56341-41-4 | C8H6FNO | 详情 | 详情 |