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

Thomas Parsons, C Ghellamallah, Louise Male, Neil Spencer, Richard Grainger

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)5021-5023
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number14
Early online date13 May 2011
DOIs
Publication statusPublished - 21 Jul 2011

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