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Indazoles: Regioselective Protection and Subsequent Amine Coupling Reactions
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2009
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DerivativesAcidic ConditionsOrganic ChemistryRegioselective Protection5-Bromoindazoles ParticipateStereoselective SynthesisChemistryPharmacologyVarious Substituted IndazolesEnantioselective Synthesis
Indazoles are unselectively protected under strongly basic conditions to give a mixture at N-1 and N-2. Under mildly acidic conditions, regioselective protection at N-2 takes place. Thermodynamic conditions lead to regioselective protection at N-1. This trend applies to various substituted indazoles. Protected 5-bromoindazoles participate in Buchwald reactions with a range of amines to generate novel derivatives.