Preparation and Reactions of 4-, 5-, and 6-Methoxy Substituted 3-Lithioindoles and 3-Indolylzinc Derivatives

M Amat, F Seffar, N Llor, J Bosch

Index: Amat; Seffar; Llor; Bosch Synthesis, 2001 , # 2 p. 267 - 275

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Citation Number: 1

Abstract

Abstract: The preparation of 4-, 5-, and 6-methoxy substituted 3-lithio-1-(trialkylsilyl) indoles 4b-d by metalation of the corresponding 3-bromoindoles, and their reactions with iodomethane, DMF, ethylene oxide and aziridines are reported. Transmetalation of 3- lithioindoles 4b-d with ZnCl2 afforded 3-indolylzinc chlorides 11b-d, which underwent Pd (0)- catalyzed cross-coupling reactions with 2-halopyridines to give 4-, 5-, and 6-methoxy ...