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Issue 14, 2011
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Regioselective dibromination of methyl indole-3-carboxylate and application in the synthesis of 5,6-dibromoindoles

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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.

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

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Publication details

The article was received on 04 Apr 2011, accepted on 12 May 2011 and first published on 13 May 2011


Article type: Communication
DOI: 10.1039/C1OB05522D
Citation: Org. Biomol. Chem., 2011,9, 5021-5023
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    Regioselective dibromination of methyl indole-3-carboxylate and application in the synthesis of 5,6-dibromoindoles

    T. B. Parsons, C. Ghellamallah, L. Male, N. Spencer and R. S. Grainger, Org. Biomol. Chem., 2011, 9, 5021
    DOI: 10.1039/C1OB05522D

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