Triethylamine → HCID 22244700, compound

Participants

Reaction Steps

To a stirred solution of [6-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)pyridin-3-yl]methanol (step 2, 1.51 g, 5.41 mmol), triethylamine (0.90 mL, 6.49 mmol), and dichloromethane (30 mL) was added methanesulfonyl chloride (0.46 mL, 5.95 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 1 h. The mixture was diluted with dichloromethane and washed with water. The organic layer was dried over MgSO4, and concentrated under reduced pressure. The residue was treated with potassium cyanide (1.76 g, 27.0 mmol), N,N-dimethylformamide (25 mL) and water (5 mL) at 65° C. for 16 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and toluene (2:1) and washed with water. The organic fraction was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with hexane/ethyl acetate (6:1) to afford 0.63 g (41%) of the title compound: MS (ESI) m/z 289 [M+H]+, 287 [M−H]−, 1H-NMR (CDCl3) δ 8.39-8.38 (1H, m), 7.94 (1H, d, J=8.6 Hz), 7.79-7.76 (1H, m), 7.46-7.29 (5H, m), 3.77 (2H, s), 2.61 (3H, s), 2.31 (3H, s).

Provenance & Evidence