Benzyl Bromide → 3-Acetyl-4-(benzylamino)-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of the product from Example 2 (50 mg), potassium carbonate (14 mg) and benzyl bromide (12 μL) in THF (2 mL) was stirred overnight. No progress of the reaction was observed. The reaction mixture was cooled to 0° C., followed by addition of sodium hydride (60% in mineral oil) (4 mg). The reaction was stirred for 10 min and benzyl bromide (12 μL) was added. The suspension was allowed to come to room temperature and stirred overnight. The reaction was quenched with water and extracted twice with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification on a preparative silica TLC plate eluted with 45% ethyl acetate in hexane afforded the title compound. HPLC/MS: 561.9 (M+1), 563.9 (M+3); Rt=5.09 min.

Provenance & Evidence