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

Participants

Reaction Steps

The title compound was prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoic 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. The reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes) to provide 81 mg (69%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.43 (s, 1H), 7.44 (m, 2H), 7.16 (m, 2H), 5.30 (dd, J=6.7, 8.6 Hz, 1H), 3.81 (ddd, J=3.2, 8.6, 11.5 Hz, 1H), 3.50 (ddd, J=3.1, 7.4, 10.2 Hz, 1H), 2.79 (dt, J=2.8, 6.3 Hz, 2H), 2.33 (m, 1H), 2.30 (s, 3H), 2.22 (m, 1H), 1.96 (m, 1H), 1.86 (m, 1H), 0.98 (t, J=7.0 Hz, 3H); MS: (ES) m/z calculated for C20H19ClF4N5O [M+H]+ 470.1, found 470.1.

Provenance & Evidence