2-[4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]propanoic 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]propan-1-one

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Reaction Steps

The title compound was prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoic 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 137 mg (75%) of the title compound as a white foam. 1H NMR (400 MHz, CDCl3) δ 8.41 (s, 1H), 7.43 (m, 2H), 7.15 (m, 2H), 5.52 (q, J=7.0 Hz, 1H), 3.75 (m, 1H), 3.41 (m, 1H), 2.81 (m, 2H), 2.28 (s, 3H), 1.85-1.99 (m, 2H), 1.81 (d, J=7 Hz, 1H); MS: (ES) m/z calculated for C20H19ClF4N5O [M+H]+ 456.1, found 456.1.

Provenance & Evidence