Tetrahydrofuran → HCID 178504738, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-{4-chloro-5-[(E)-1-[3-chloro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethenyl]-1H-imidazol-2-yl}pyridine (1.10 g) in a mixed solvent of tetrahydrofuran (10 mL), methanol (10 mL) and water (10 mL) was added Oxone (registered trade mark) (3.02 g) under ice-cooling, and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the residue in a mixed solvent of acetonitrile (20 mL) and water (10 mL) was added sodium percarbonate (772 mg) under ice-cooling. The reaction solution was warmed to room temperature, and the mixture was stirred at room temperature for 3 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-100:0, volume ratio) to give the title compound (0.471 g, yield 40%) as a colorless amorphous solid. MS: 478 (MH+).

Provenance & Evidence