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

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Reaction Steps

The compound was prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic 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 2×1 M NaHSO4 and 2×1.5 M KOH and the organics were eluted through a silica plug. The resulting slurry was concentrated to a white solid that was triturated with 1:1 hexanes:EtOAc to give the title compound as a crystalline white solid (75.9 mg). 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.34 (s, 0.7H), 7.57 (s, 0.3H), 7.44 (m, 2H), 7.15 (m, 2H), 5.24 (s, 0.4H), 5.13 (s, 1.6H), 3.92 (m, 0.5H), 3.84 (m, 1.5H), 2.87 (m, 2H), 2.33 (s, 2.3H), 2.32 (s, 0.7H), 2.12 (m, 1.5H), 2.05 (m, 0.5H); MS: (ES) m/z calculated for C19H17ClF4N5O [M+H]+ 442.1, found 442.0.

Provenance & Evidence