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Issue 14, 2011

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

Supplementary files

Article information


Submitted
04 Apr 2011
Accepted
12 May 2011
First published
13 May 2011

Org. Biomol. Chem., 2011,9, 5021-5023
Article type
Communication

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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