Scalable Synthesis of Trifluoromethylated Imidazo-Fused N-Heterocycles Using TFAA and Trifluoroacetamide as CF₃-Reagents

Gabriel Schäfer*, Muhamed Ahmetovic and Stefan Abele

*Process Chemistry R&D, Idorsia Pharmaceuticals Ltd., Hegenheimermattweg 91, CH-4123 Allschwil, Switzerland, Email: gabriel.schaeferidorsia.com

G. Schäfer, M. Ahmetovic, S. Abele, Org. Lett., 2017, 19, 6578-6581.

DOI: 10.1021/acs.orglett.7b03291

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Abstract

Heterocyclic benzylamines can be reacted with TFAA as trifluoromethylating reagent to provide imidazo-fused N-heterocycles. Alternatively, a two-step synthesis of trifluoromethylated imidazo-fused N-heterocyles from heterocyclic benzyl (pseudo)halides using trifluoroacetamide as trifluoromethylating reagent proceeds via alkylation followed by dehydrative cyclization.

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Key Words

imidazo[1,5-a]pyridines

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ID: J54-Y2017