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Short Paper | Regular issue | Vol 96, No. 6, 2018, pp.1067-1074
Published online, 8th May, 2018
DOI: 10.3987/COM-18-13893
■ A Practical Synthesis of 2-Substituted 5-Bromoindoles

Yang He, Lianlian Fan, Haoting Zhu, Xiaolin Li, Pu Zhou, and Yu Luo*

*Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241, China

Abstract

This paper describes a non-cryogenic synthetic procedure for a variety of 2-substituted 5-bromoindoles. The direct magnesiation of 5- bromo-1-(4-toluenesulfonyl)indole with a mixture of i-PrMgCl/LiCl and diisopropylamine allows for the preparation of various 2-substituted indoles. The advantages of this procedure include the non-cryogenic conditions, simple operations and inexpensive Grignard reagents. In addition, this procedure is especially advantageous for the preparation of 2,5-dibromoindole with reduced synthetic steps, low production cost and good overall yields.