Tetrahedron

A highly effective synthesis of 2-alkynyl-7-azaindoles: Pd/C-mediated alkynylation of heteroaryl halides in water

M Layek, V Gajare, D Kalita, A Islam, K Mukkanti, M Pal

Index: Layek, Mohosin; Gajare, Vikas; Kalita, Dipak; Islam, Aminul; Mukkanti; Pal, Manojit Tetrahedron, 2009 , vol. 65, # 25 p. 4814 - 4819

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Citation Number: 19

Abstract

The reaction of 4-chloro-2-iodo-7-azaindole with terminal alkynes was investigated using 10% Pd/C–PPh3–CuI as a catalyst system in water. This study afforded a new, mild and selective process for the preparation of 2-alkynyl-4-chloro-7-azaindole in good yields via C– C bond forming reaction. The resulting chloro derivative can be functionalized further via another Pd-mediated C–C bond forming reaction with arylboronic acid.