Tetrahedron letters

Deprotection of N-tosylated indoles and related structures using cesium carbonate

JS Bajwa, GP Chen, K Prasad, O Repič, TJ Blacklock

Index: Bajwa, Joginder S.; Chen, Guang-Pei; Prasad, Kapa; Repic, Oljan; Blacklock, Thomas J. Tetrahedron Letters, 2006 , vol. 47, # 36 p. 6425 - 6427

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Citation Number: 49

Abstract

Most of these methods, while effective in a number of cases, have serious incompatibilities with other functional groups. While making an indole derived drug substance, we needed to effect N-detosylation. Several literature methods were tried which invariably gave low yields due to the formation of many by-products. This led to the development of a new and a very mild method for N-detosylation of indoles and related structures using cesium carbonate (Scheme 1). ...

~90%

~86%

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