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






Organic & Biomolecular Chemistry 9(14): 5021-5023

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

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.


Accession: 055445622

PMID: 21643565

DOI: 10.1039/c1ob05522d



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