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Palladium-Catalyzed Synthesis of Free-NH Indole 2-Acetamides and Derivatives from Ethyl 3-(o-Trifluoroacetamidoaryl)-1-propargylic Carbonates
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2009
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Chemical EngineeringEngineeringFree-nh Indole 2-AcetamidesOrganic ChemistryEthyl 3-Organometallic CatalysisCatalysisChemistry-1-Propargylic CarbonatesPalladium-catalyzed SynthesisSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringCarbon Monoxide
The reaction of ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates with primary or secondary amines in the presence of Pd2(dba)3, dppf, and carbon monoxide in THF at 80 ˚C provides ready access to free-NH indole 2-acetamides. The reaction can be applied to the synthesis of free-NH indole 2-acetic acid methyl esters.