Diphenyl sulfide → HCID 68433593, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-{5-[(E)-1-[3-chloro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethenyl]-4-iodo-1H-imidazol-2-yl}pyridine (0.340 g) in a mixed solvent of tetrahydrofuran (3 mL), methanol (3 mL) and water (3 mL) was added Oxone (registered trade mark) (777 mg) 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 (10 mL) and water (5 mL) was added sodium percarbonate (198 mg) under ice-cooling. The reaction solution was warmed to room temperature, and the mixture was stirred at room temperature for 2 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=50:50-100:0, volume ratio) to give a colorless oil. To a solution of the obtained oil in methanol (5 mL) were added 10% palladium carbon (30 mg), diphenylsulfide (0.7 μL) and triethylamine (0.29 mL). The reaction solution was purged with hydrogen, and stirred at room temperature for 16 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0, volume ratio) and recrystallized from hexane-ethyl acetate to give the title compound (0.047 g, yield 17%) as colorless crystals. melting point 106-109° C. MS: 446 (MH+).

Provenance & Evidence