Sodium Iodide → 7-(1,3-dimethyl-1H-pyrazol-5-yl)-3-(3-((4-methyl-5-(2-methyl-5-quinolinyl)-4H-1,2,4-triazol-3-yl)thio)propyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine (4 g) (intermediate 3) in dimethylformamide, at room temperature, 5-{5-[(3-chloropropyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl}-2-methylquinoline (intermediate 8) (6.8 g), sodium iodide (3.06 g) and anhydrous potassium carbonate (2.82 g) were subsequently added and the reaction mixture was warmed to 60° C. and kept reacting for 24 h. After allowing the reaction mixture to reach room temperature, water (70 ml) was added and the reaction mixture was extracted twice with ethyl acetate (50 ml×2). The organic phase was dried with sodium sulphate and after evaporation the crude product was purified by chromatography on silica gel with 100-95% dichloromethane-methanol elution to give the title compound (3.3 g) as a pale yellow solid.

Provenance & Evidence