Tetrahedron

Efficient syntheses of 2-(3′, 5′-difluorophenyl)-3-(4′-methylsulfonylphenyl) cyclopent-2-enone, a potent COX-2 inhibitor

…, EJJ Grabowski, PJ Reider, C Black, N Ouimet, P Prasit

Index: Zhao, Dalian; Feng, Xu; Chen, Cheng-yi; Tillyer, Rich D.; Grabowski, Edward J. J.; Reider, Paul J.; Black, Cameron; Quimet, Nathalie; Prasit, Peppi Tetrahedron, 1999 , vol. 55, # 19 p. 6001 - 6018

Full Text: HTML

Citation Number: 25

Abstract

2-(3′, 5′-Difluorophenyl)-3-(4′-methylsulfonylphenyl) cyclopent-2-enone (1) displays high selectivity and potency against COX-2. Three efficient syntheses of this diarylcyclopentenone are described. The first approach employs a Suzuki coupling reaction as the key step while the second synthesis features an intramolecular Friedel-Crafts acylation. The third, and preferred route to this compound involves a sequential malonate ...