Synthesis and applications of 3-bromo-2-hydroxy-1-tosylazaindolines

Herein we describe a practical synthetic method for 3-bromo-2-hydroxy-1-tosylazaindolines and 2hydroxy-1-tosylazaindoline-3-triethylammonium bromides. 3-Bromo-2-hydroxy-1-tosylazaindolines were found to be stable crystals and could be stored at ambient temperature without consideration of moisture in the air. These indolines are useful reagents for the formal C3-electrophilic reactions of azaindoles with various nucleophiles. We used this method to synthesize various key intermediates of biologically active 3-substituted 7-azaindole derivatives. (c) 2021 Elsevier Ltd. All rights reserved.

Automated summary

This study presents a practical synthetic method for 3-bromo-2-hydroxy-1-tosylazaindolines and 2hydroxy-1-tosylazaindoline-3-triethylammonium bromides, which are stable crystals useful in the synthesis of biologically active 3-substituted 7-azaindole derivatives.