Water → {2-[1-acetyl-3-(2,5-difluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-5-yl]ethyl}(dimethyl)silanol

Participants

Reaction Steps

To a solution of 100 mg (0.31 mmol) of 1-4 in 1 mL of toluene was added 51 μL (0.46 mmol) of chlorodimethylsilane and 13 mg (0.03 mmol) of hydrogen hexachloroplatinate(IV) hydrate. The reaction mixture was heated at 85° C. for 18 hours in a sealed tube before 500 μL of water was added. Heating was continued for 15 minutes then the reaction was cooled to room temperature, dumped into a separatory funnel containing EtOAc, washed successively with water, brine, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with EtOAc/hexanes to provide 1-5 as a white solid. Data for 1-5: 1HNMR (500 MHz, CDCl3) δ 7.65 (m, 1H), 7.25 (m, 5H), 7.0 (m, 2H), 3.6-3.3 (m, 2H), 2.9 (m, 1H), 2.4 (m, 3H), 2.15 (m, 1H), 0.6-0.3 (m, 2H), 0.15 (m, 6H) ppm. HRMS (MALDI) calc'd M+H for C21H24F2N2O2Si: 403.1648 Found: 403.1637.

Provenance & Evidence