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

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