Sequential Sonogashira and Suzuki Cross-Coupling Reactions in the Indole and Indazole Series

Bernhard Witulski; Javier Ramon Azcon; Carole Alayrac; Anca Arnautu; Valérie Collot; Sylvain Rault

doi:10.1055/s-2005-861825

PAPER

Sequential Sonogashira and Suzuki Cross-Coupling Reactions in the Indole and Indazole Series

Bernhard Witulski*^a, Javier Ramon Azcon, Carole Alayrac^a, Anca Arnautu^b, Valérie Collot^b, Sylvain Rault*^b
^a Westfälische Wilhelms-Universität Münster, Organische Chemie Institut, Correnstr. 40, 48143 Münster, Germany
Fax: +49(251)8336501; e-Mail: witulski@uni-muenster.de;
^b CERMN, UFR des Sciences Pharmaceutiques, 5 rue Vaubénard, 14032 Caen cedex, France

Abstract

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Abstract

3-Iodoindoles, 5-bromo-3-iodoindoles and 5-bromo-3-iodoindazoles have been studied with respect to their reactivity and selectivity in palladium catalyzed Sonogashira and Suzuki cross-coupling reactions. As a result, sequential Sonogashira-Sonogashira, Sonogashira-Suzuki, and Suzuki-Sonogashira reactions with 5-bromo-3-iodoindoles or indazoles were used to obtain a large range of new functionalized indoles and indazoles, which are potential 5-HT receptor ligands.

Key words

palladium - catalysis - alkynes - indoles - indazoles

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References

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In our hands, application of this protocol to our substrates has not been satisfactory so far.