A Scalable Synthesis of a 1,7-Naphthyridine Derivative, a PDE-4 Inhibitor

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• 作者：Xinglong Jiang ; George T. Lee ; Edwin B. Villhauer ; Kapa Prasad ; Mahavir Prashad
• 刊名：Organic Process Research & Development
• 出版年：2010
• 出版时间：July 16, 2010
• 年：2010
• 卷：14
• 期：4
• 页码：883-889
• 全文大小：252K
• 年卷期：v.14,no.4(July 16, 2010)
• ISSN：1520-586X

文摘

A six-step synthesis of a 4-[8-(3-fluorophenyl)[1,7]naphthyridin-6-yl]-trans-cyclohexanecarboxylic acid with an overall yield of 27% starting from 2-cyano-3-methylpyridine, cyclohexane-1,4-dicarboxylic acid dimethyl ester, and 3-fluorophenylboronic acid is described. The trans stereochemistry in the cyclohexane moiety was achieved through a series of equilibration steps at different stages of the synthesis.