Robust Synthesis of Methyl 5-Chloro-4-fluoro-1 H-indole-2-carboxylate: A Key Intermediate in the Preparation of an HIV NNRTI Candidate

…, NC Chaudhuri, CP Hencken, F Jeannot…

文献索引：Mayes, Benjamin A.; Chaudhuri, Narayan C.; Hencken, Christopher P.; Jeannot, Frederic; Latham, G. Mark; Mathieu, Steven; Mcgarry, F. Patrick; Stewart, Alistair J.; Wang, Jingyang; Moussa, Adel Organic Process Research and Development, 2010 , vol. 14, # 5 p. 1248 - 1253

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被引用次数: 10

摘要

A synthetic preparation of methyl 5-chloro-4-fluoro-1 H-indole-2-carboxylate, a key intermediate towards phosphoindole inhibitors of HIV non-nucleoside reverse transcriptase, is described. The five-step synthesis involved Boc protection of the commercially available 4- chloro-3-fluoroaniline and regioselective iodination at C-2. After facile Boc deprotection, cyclization of the resultant o-iodoaniline gave the corresponding 5-chloro-4-fluoro-indole- ...