Access to Highly Substituted 7-Azaindoles from 2-Fluoropyridines via 7-Azaindoline Intermediates
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- 作者：Philippe Nuhant ; Christophe Allais ; Ming Z. Chen ; Jotham W. Coe ; Alpay Dermenci ; Olugbeminiyi O. Fadeyi ; Andrew C. Flick ; James J. Mousseau
- 刊名：Organic Letters
- 出版年：2015
- 出版时间：September 4, 2015
- 年：2015
- 卷：17
- 期：17
- 页码：4292-4295
- 全文大小：432K
- ISSN：1523-7052
文摘
A versatile synthesis of 7-azaindoles from substituted 2-fluoropyridines is described. C3-metalation and 1,4-addition to nitroolefins provide substituted 2-fluoro-3-(2-nitroethyl)pyridines. A facile oxidative Nef reaction/reductive amination/intramolecular SNAr sequence furnishes 7-azaindolines. Finally, optional regioselective electrophilic C5-substitution (e.g., bromination or nitration) and subsequent in situ oxidation delivers highly functionalized 7-azaindoles in high overall efficiency.