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Preparation of the HIV Attachment Inhibitor BMS-663068. Part 4. Synthesis of the 6-Azaindole Core

2017; American Chemical Society; Volume: 21; Issue: 8 Linguagem: Inglês

10.1021/acs.oprd.7b00152

1520-586X

Michael Bultman, Junying Fan, Dayne Fanfair, Michelle Soltani, James H. Simpson, Saravanababu Murugesan, Maxime Soumeillant, Ke Chen, Christina A. Risatti, Thomas E. La Cruz, Frédéric G. Buono, Victor Hung, Richard L. Schild, Sabrina Ivy, Jason T. Sweeney, David A. Conlon, Martin D. Eastgate,

Synthesis of Indole Derivatives

We report research focused on the construction of the 6-azaindole core, a key intermediate in the synthesis of the clinical candidate BMS-663068. The work describes an efficient and scalable method to access the 6-azaindole from a protected 3-ketopyrrole via a Pictet–Spengler cyclization and a radical-mediated aromatization. The process reported herein has been successfully implemented on the multikilogram scale to support preclinical development and clinical studies of BMS-663068.