2-Pyridinecarboxaldehyde → HCID 59331599, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{4-[(3-methoxypropyl)sulfonyl]phenyl}-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.450 g) in ethanol (20 mL) were added pyridine-2-carbaldehyde (0.135 mL), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (35 mg) and triethylamine (0.071 mL), and the mixture was heated under reflux for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-100:0, volume ratio) to give a colorless oil. To a solution of the obtained oil in acetic acid (10 mL) was added ammonium acetate (355 mg), and the mixture was stirred at 110° C. for 1.5 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium 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 (0.400 g, yield 72%) as a colorless amorphous solid. MS: 425 (MH+).

Provenance & Evidence