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

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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.


Original languageEnglish
Pages (from-to)5021-5023
Number of pages3
JournalOrganic and Biomolecular Chemistry
Issue number14
Publication statusPublished - 1 Jan 2011