Organic & Biomolecular Chemistry 2011-07-21

Regioselective dibromination of methyl indole-3-carboxylate and application in the synthesis of 5,6-dibromoindoles.

Thomas B Parsons, Cédric Ghellamallah, Louise Male, Neil Spencer, Richard S Grainger

Index: Org. Biomol. Chem. 9(14) , 5021-3, (2011)

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Abstract

Treatment of methyl indole-3-carboxylate with bromine in acetic acid gives methyl 5,6-dibromoindole-3-carboxylate regioselectively, from which the parent 5,6-dibromoindole can be accessed via a one-pot, microwave-mediated ester hydrolysis and decarboxylation. Application of these building blocks in syntheses of natural and non-natural 5,6-dibromoindole derivatives, including meridianin F and 5,6-dibromo-2'-demethylaplysinopsin, is reported.