(2-(trifluoromethyl)phenyl)acetic acid → 1-(1-(4-fluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)-2-(2-(trifluoromethyl)phenyl)ethanone

Participants

Reaction Steps

The compound was prepared from 2-trifluoromethylphenylacetic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method B. The product mixture was washed with 1 M NaHSO4. The reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes) to provide 72 mg (59%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.46 (s, 0.8H), 7.70 (m, 1H), 7.55 (m, 1.2H), 7.41-7.50 (m, 4H), 7.15 (m, 2H), 4.19 (s, 0.3H), 4.06 (s, 1.7H), 3.95 (m, 0.3H), 3.76 (m, 1.7H), 2.82-2.88 (m, 2H), 2.03 (m, 2H); MS: (ES) m/z calculated for C21H18F4N3O [M+H]+ 404.1, found 404.1.

Provenance & Evidence