1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine → HCID 73335540, compound

Participants

Reaction Steps

The title compound was prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-3-methylbutanoic 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 89 mg (74%) of the title compound as a glassy white solid. 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 7.44 (m, 2H), 7.16 (m, 2H), 5.03 (d, J=10.9 Hz, 1H), 3.89 (ddd, J=2.7, 8.2, 10.9 Hz, 1H), 3.78 (ddd, J=2.7, 7.8, 10.9 Hz, 1H), 2.96 (m, 1H), 2.79 (m, 2H), 2.37 (s, 3H), 1.99 (m, 1H), 1.82 (m, 1H), 1.12 (d, J=6.3 Hz, 3H), 0.79 (d, J=7.1 Hz, 3H); MS: (ES) m/z calculated for C22H23ClF4N5O [M+H]+ 484.1, found 484.1.

Provenance & Evidence