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

Mercedes Amat; Fátima Seffar; Núria Llor; Joan Bosch

doi:10.1055/s-2001-10812

Synthesis 2001; 2001(2): 0267-0275
DOI: 10.1055/s-2001-10812

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

Mercedes Amat^* , Fátima Seffar, Núria Llor, Joan Bosch

^*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain; Fax +34(93)4024539; E-mail: amat§farmacia.far.ub.es

Abstract

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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 substituted 3-(2-pyridyl)indoles.

indoles - lithium - zinc - cross-coupling - pyridylindoles - silyl protecting groups

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