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

Participants

Reaction Conditions

Reaction Steps

2-Chloro-1-(1-(4-fluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)ethanone (118 mg, 0.4 mmol) was diluted in 1.2 mL of 2:1 THF:DMF and treated with K2CO3 (111 mg, 0.8 mmol) and 5-methyl-3-(trifluoromethyl)-1H-pyrazole (60 mg, 0.4 mmol). The slurry was heated to 75° C. for 2 hours. The reaction slurry was purified by normal phase flash chromatography (24 g column, eluting with 10-80% EtOAc in hexanes) to provide 109 mg (67%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.36 (s, 0.8H), 7.59 (s, 0.2H), 7.42-7.47 (m, 2H), 7.12-7.25 (m, 2H), 5.25 (s, 0.4H), 5.14 (s, 1.6H), 3.92 (m, 0.4H), 3.86 (m, 1.6H), 2.86 (t, J=6.2 Hz, 2H), 2.37 (s, 2.4H), 2.36 (m, 0.6H), 2.11 (m, 1.6H), 2.04 (m, 0.4H); MS: (ES) m/z calculated for C19H18F4N5O [M+H]+ 408.1, found 408.1.

Provenance & Evidence