4.4 Article

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

Journal

TETRAHEDRON
Volume 97, Issue -, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132404

Keywords

3-Bromo-2-hydroxy-1-tosylazaindoline; 2-Hydroxy-1-tosylazaindoline-3-triethylammonium bromide; C3-electrophilic reagent; 3-Substituted 7-azaindole; 7-Azaindole-3-acetic acid

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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.
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.

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