Facile Reductive Amination of Aldehydes with Electron-Deficient Anilines by Acyloxyborohydrides in TFA: Application to a Diazaindoline Scale-Up

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• 作者：Eric E. Boros ; James B. Thompson ; Subba R. Katamreddy ; Andrew J. Carpenter
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：May 1, 2009
• 年：2009
• 卷：74
• 期：9
• 页码：3587-3590
• 全文大小：140K
• 年卷期：v.74,no.9(May 1, 2009)
• ISSN：1520-6904

文摘

A scale-up of diazaindoline 1 was achieved in four stages and 32% overall yield. The key step involved rapid reductive amination of aldehyde 8 with aniline 5 by sodium triacetoxyborohydride (STAB-H) and TFA followed by ring closure of intermediate amine 9 to compound 1 in the same pot. These reaction conditions were also applied to facile reductive aminations with anilines known to have little reactivity under STAB-H/AcOH conditions. Spectral data supported the tris(trifluoroacetoxy)borohydride anion (16) as the active reducing agent.