Sodium Carbonate → 4-[1-(2,4-dichlorophenyl)-3-[(4-hydroxy-4-phenylpiperidin-1-yl)carbonyl]-4-methyl-1H-pyrazol-5-yl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

Nitrogen gas was bubbled through a solution of 1-{[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl}-4-phenylpiperidin-4-ol (1 eq., 45 mg, 0.077 mmol), K4[Fe(CN)6].3H2O (0.22 eq., 7.5 mg, 0.017 mmol), sodium carbonate (1 eq., 8.1 mg, 0.017 mmol), and palladium(II) acetate (0.10 eq., 1.7 mg, 0.008 mmol) in N,N-dimethylacetamide (2 mL) for 1 min. The solution is capped and stirred at 120° C. for 16 h. The reaction was concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-100% ethyl acetate/hexane to yield pure 4-[1-(2,4-dichlorophenyl)-3-[(4-hydroxy-4-phenylpiperidin-1-yl)carbonyl]-4-methyl-1H-pyrazol-5-yl]benzonitrile (4 mg, 10%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.75-1.94 (m, 2H) 2.07-2.32 (m, 5H) 3.25-3.43 (m, 1H) 3.55-3.76 (m, 1H) 4.31 (d, J=12.90 Hz, 1H) 4.73 (d, J=13.00 Hz, 1H) 7.01 (d, J=8.48 Hz, 2H) 7.08-7.57 (m, 10H).

Provenance & Evidence