Nitrogen → 6-(4-(1-(4,5-dihydrooxazol-2-yl)cyclopropyl)phenyl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)-5,6-dihydro-1H-pyrazolo[3,4-c]pyridin-7(4H)-one

Participants

Reaction Steps

Part B. The product from Part A (75.2 mg, 0.240 mmol) and 1-(4-methoxyphenyl)-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (76.8 mg, 0.247 mmol) were dissolved in DMSO (0.5 mL). Potassium carbonate (0.109 g, 0.788 mmol), copper iodide (spatula tip), and 1,10-phenanthroline (spatula tip) were added and the reaction was heated to 120° C. for 12 h under an environment of N2. The reaction was cooled, diluted with EtOAc, washed with H2O (2×), brine, dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (silica, 100% EtOAc) afforded the title compound. LC/MS (ESI+) 497.6 (M+H), tR=2.44 min (10–90% CH3CN/H2O in a 4-min run). 1H NMR ((CD3)2CO, 300 MHz) δ 7.51 (d, J=9.0 Hz, 2H), 7.32 (AA′BB′, J=8.4 Hz, 4H), 6.97 (d, J=9.0 Hz, 2H), 4.16 (m, 4H), 3.82 (s, 3H), 3.67 (t, J=9.2 Hz, 2H), 3.17 (t, J=6.6 Hz, 2H), 2.02 (m, 2H), 1.42 (m, 2H), 1.17 (m, 2H) ppm.

Provenance & Evidence