Regioselective Synthesis of 4- and 7-Alkoxyindoles from 2,3-Dihalophenols: Application to the Preparation of Indole Inhibitors of Phospholipase A2

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• 作者：Roberto Sanz ; M. Pilar Castroviejo ; Veró ; nica Guilarte ; Antonio Pé ; rez ; Francisco J. Fañ ; an&aacute ; s
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：July 6, 2007
• 年：2007
• 卷：72
• 期：14
• 页码：5113 - 5118
• 全文大小：127K
• 年卷期：v.72,no.14(July 6, 2007)
• ISSN：1520-6904

文摘

An efficient and regioselective synthesis of 4- and 7-alkoxyindoles has been developed from commerciallyavailable starting materials such as 3-halophenols and 3-chloroanisole. Directed ortho-metalation followedby two palladium-catalyzed processes, a Sonogashira coupling and a tandem amination/cyclization reaction,allows the synthesis of regiochemically pure 4- and 7-substituted indoles. This strategy has beensuccessfully applied to the preparation of 2-[3-(2-amino-2-oxoacetyl)-1-benzyl-2-ethyl-1H-indol-4-yloxy]acetic acid (LY315920), a known inhibitor of phospholipase A₂.