Phenacyl bromide → (4-([(4-Phenyl-1,3-thiazol-2-yl)(2-pyridin-2-ylethyl)amino]methyl}phenyl)methanol

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Reaction Steps

A mixture of 2-bromo-1-phenylethanone (1.0 g), N-(2-pyridin-2-ylethyl)thiourea (0.90 g) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 1 hr. Sodium hydride (60% in oil, 400 mg) was added to the reaction mixture and the mixture was further stirred at room temperature for 1 hr. Methyl 4-(bromomethyl)benzoate (1.15 g) was added to the reaction mixture under ice-cooling, and the mixture was allowed to warm to room temperature and further stirred for 1 hr. The reaction mixture was poured into aqueous sodium dihydrogenphosphate solution and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give a yellow oil. The yellow oil was dissolved in tetrahydrofuran (30 mL) and lithium aluminum hydride (120 mg) was added by small portions under ice-cooling. The reaction mixture was stirred under ice-cooling for 30 min and sodium sulfate 10 hydrate (1.0 g) was added. The mixture was allowed to warm to room temperature and stirred for 30 min. The resulting precipitate was filtered off and the filtrate was concentrated to give the title compound (890 mg, yield 44%) as a yellow oil.

Provenance & Evidence