Methyl iodide → 5-[2-(4-bromo-2-chloro-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of the 5-[2-(4-bromo-2-chloro-phenyl)-acetyl]-1-methyl-1H-pyridin-2-one obtained in step 1 (583 mg) in tetrahydrofuran (12 ml) was added sodium hydride (60% dispersion in mineral oil, 72 mg). The mixture was stirred at room temperature for 2 h and at 40° C. for 30 min. The mixture was cooled in an ice bath. Methyl iodide (267 mg) was added dropwise. After 10 min the ice bath was removed and the mixture was stirred at room temperature for 4 h. Sodium hydride (60% dispersion in mineral oil, 35 mg) and methyl iodide (121 mg) were added and the mixture was stirred overnight at room temperature. The reaction was quenched with ice water and extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 7:3=>0:1) to give the title compound (353 mg) as a colorless foam. MS (m/e, ISP neg. ion)=352.0 [M−H+].

Provenance & Evidence