Synthesis of the 6-Azaindole Containing HIV-1 Attachment Inhibitor Pro-Drug, BMS-663068
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- 作者：Ke Chen ; Christina Risatti ; Michael Bultman ; Maxime Soumeillant ; James Simpson ; Bin Zheng ; Dayne Fanfair ; Michelle Mahoney ; Boguslaw Mudryk ; Richard J. Fox ; Yi Hsaio ; Saravanababu Murugesan ; David A. Conlon ; Frederic G. Buono ; Martin D. Eastgate
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：September 19, 2014
- 年：2014
- 卷：79
- 期：18
- 页码：8757-8767
- 全文大小：706K
- ISSN：1520-6904
文摘
The development of a short and efficient synthesis of a complex 6-azaindole, BMS-663068, is described. Construction of the 6-azaindole core is quickly accomplished starting from a simple pyrrole, via a regioselective Friedel鈥揅rafts acylation, Pictet鈥揝pengler cyclization, and a radical-mediated aromatization. The synthesis leverages an unusual heterocyclic N-oxide 伪-bromination to functionalize a critical C鈥揌 bond, enabling a highly regioselective copper-mediated Ullmann鈥揋oldberg鈥揃uchwald coupling to install a challenging triazole substituent. This strategy resulted in an efficient 11 step linear synthesis of this complex clinical candidate.