Diisopropylethylamine → 2-[2-chloro-4-(trifluoromethyl)phenyl]-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone

Participants

Reaction Steps

To a mixture of 2-[2-chloro-4-(trifluoromethyl)phenyl]acetic acid (59 mg, 0.23 mmol) and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (50 mg, 0.23 mmol) in DMF (1 mL) was added Hunig's base (59 mg, 0.46 mmol) and 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uranium hexafluorophosphate methanaminium (HATU) (96 mg, 0.2 mmol). The mixture was stirred at room temperature for 1 hour, and then was partitioned between water (4 mL) and ethyl acetate (6 mL). The organic layer was washed with brine and dried (Na2SO4), filtered, concentrated in vacuo, and purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give the desired product as a white solid (25 mg, 25%). 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 0.8H), 7.70 (s, 1H), 7.56-7.44 (m, 4H), 7.38 (s, 0.2H), 7.18-7-14 (m, 2H), 4.14 (s, 2H), 3.82 (m, 2H), 2.85 (m, 2H), 2.08 (m, 2H); MS: (ES) m/z calculated for C21H16ClF4N3O [M+H]+ 438.1, found 438.1.

Provenance & Evidence