title: Regioselective dibromination of methyl indole-3-carboxylate and application in the synthesis of 5,6-dibromoindoles.
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.
authors.affiliation: School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK.
authors.forename: Thomas B
authors.initials: TB
authors.lastname: Parsons
authors.forename: Cédric
authors.initials: C
authors.lastname: Ghellamallah
authors.forename: Louise
authors.initials: L
authors.lastname: Male
authors.forename: Neil
authors.initials: N
authors.lastname: Spencer
authors.forename: Richard S
authors.initials: RS
authors.lastname: Grainger
mesh_terms: D019342:Acetic Acid / Q000737:chemistry; D001966:Bromine / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D019342:Acetic Acid; D001966:Bromine