1-methyl-1H-imidazole-4-sulfonyl chloride → 2-(2-(1-Methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropanenitrile

Participants

Reaction Steps

To a solution of 0.135 mmol 3-phenyl-2-(1,2,3,4-tetrahydroisoquinolin-7-yl)propanenitrile in 2 ml CH2Cl2 were added 0.203 mmol DMAP and 0.162 mmol 1-methyl-1H-imidazole-4-sulfonyl chloride. The mixture was stirred at room temperature for 3 h. Additional 0.162 mmol 1-methyl-1H-imidazole-4-sulfonyl chloride were added and the mixture was stirred for 3 d. The mixture was diluted with CH2Cl2 and washed with 1N HCl, saturated NaHCO3 and H2O. The combined aqueous layers were extracted with CH2Cl2. The combined organic phase was dried over MgSO4 and filtered. Evaporation of the solvent gave 90 mg of the crude material. The material was purified by flash chromatography to yield 53 mg of a white solid (97%).

Provenance & Evidence