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

被引：4

作者：

Bultman, Michael S. ^{[1
]}

Fan, Junying ^{[1
]}

Fanfair, Dayne ^{[1
]}

Soltani, Michelle ^{[1
]}

Simpson, James ^{[1
]}

Murugesan, Saravanababu ^{[1
]}

Soumeillant, Maxime ^{[1
]}

Chen, Ke ^{[1
]}

Risatti, Christina ^{[1
]}

La Cruz, Thomas E. ^{[1
]}

Buono, Frederic G. ^{[1
]}

Hung, Victor ^{[1
]}

Schild, Richard L. ^{[1
]}

Ivy, Sabrina ^{[1
]}

Sweeney, Jason T. ^{[1
]}

Conlon, David A. ^{[1
]}

Eastgate, Martin D. ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Chem & Synthet Dev, One Squibb Dr, New Brunswick, NJ 08903 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2017年 / 21卷 / 08期

关键词：

VINYL GRIGNARD-REAGENTS; HYDROPEROXIDE; DECOMPOSITION; DERIVATIVES;

D O I：

10.1021/acs.oprd.7b00152

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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 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.

引用

页码：1131 / 1136

页数：6

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