The Expedient Synthesis of 4,2‘-Difluoro-5‘-(7-trifluoromethyl- imidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile, a GABA α2/3 Agonist

The Expedient Synthesis of 4,2‘-Difluoro-5‘-(7-trifluoromethyl- imidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile, a GABA α2/3 Agonist

An expedient regioselective synthesis of a GABA α2/3 agonist 1 is described. The key step is an efficient regioselective palladium-catalyzed coupling of 7-trifluoromethylimidazo[1,2-a]pyrimidine (5) to 5‘-chloro-4,2‘-difluorobiphenyl-2-carbonitrile (15). The efficiency of this step was affected by t...

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Veröffentlicht in:Organic process research & development 2006-05, Vol.10 (3), p.398-402
Hauptverfasser: Cameron, Mark, Foster, Bruce S, Lynch, Joseph E, Shi, Yao-Jun, Dolling, Ulf-H
Format: Artikel
Sprache:eng
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Zusammenfassung:An expedient regioselective synthesis of a GABA α2/3 agonist 1 is described. The key step is an efficient regioselective palladium-catalyzed coupling of 7-trifluoromethylimidazo[1,2-a]pyrimidine (5) to 5‘-chloro-4,2‘-difluorobiphenyl-2-carbonitrile (15). The efficiency of this step was affected by the choice of solvent, ligand, and tetrabutylammonium salt additive.
ISSN:1083-6160
1520-586X
DOI:10.1021/op050217j