Methyl iodide → Methyl 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

Participants

Reaction Steps

To a stirred solution of methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (80 mg, 0.15 mmol) in dry DMF (3 mL) was added K2CO3 (42 mg, 0.30 mmol) and methyl iodide (22 mg, 0.15 mmol, a solution in 100 μL of DMF) at 0° C. The reaction mixture was allowed to warm to room temperature and stirring was continued for 4 h. The reaction mixture was diluted with MTBE and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo to give crude product. The crude material was purified by flash chromatography (gradient from 0% to 2% MeOH/CHCl3) to provide the title compound (65 mg, 79%). 1H NMR (CD3OD) δ 8.25-8.00 (m, 2H), 7.92-7.00 (m, 6H), 4.80-4.60 (m, 2H), 4.02 (s, 3H), 3.70-3.40 (m, 6H), 3.01 (s, 3H), 2.90-2.80 (m, 2H), 1.60-1.50 (m, 4H), 1.50-1.30 (m, 4H), 1.05-0.90 (m, 6H); MS(ESI+) m/z 531.4 (M+H)+.

Provenance & Evidence