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Synthesis 2010(4): 619-630  
DOI: 10.1055/s-0029-1218585
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 5-Aryl- and 5-Heteroaryl-7-carboxyl-8-hydroxyquinaldines through Suzuki Cross-Coupling Reaction with Potassium Organotrifluoroborates

Faten Sliman, Didier Desmaële*
Université Paris-Sud, Faculté de Pharmacie, UMR CNRS 8076, 5 Rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France
Fax: +33(1)46835752; e-Mail: didier.desmaele@u-psud.fr;
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Publication History

Received 5 August 2009
Publication Date:
07 December 2009 (online)

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Abstract

A series of 5-aryl- and 5-heteroaryl-7-carboxyl-8-hydroxyquinaldines were prepared from 5-bromo-7-methoxycarbonyl-8-benzyloxyquinaldine based on the Suzuki cross-coupling reaction using potassium organotrifluoroborates. An efficient method of deprotection of the 8-hydroxy group using a microwave-assisted­ hydrogen transfer reaction is reported.

Key words

quinolines - cross-coupling - boron - palladium - arylations

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