Potassium Carbonate → HCID 59190882, compound

Participants

Reaction Steps

Dissolved 3,4-dimethoxy-N-[3-(1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide (50.0 mg, 0.12 mmol) in 1 mL of DMF. Added 2-bromo-1,1-difluoro-ethane and (0.02 mL, 0.20 mmol) K2CO3 (50.0 mg, 0.36 mmol). The mixture was stirred at room temperature overnight. LC-MS indicated low conversion to alkylated product. Heated the mixture to 60° C. for 8 h with continued low conversion, thereafter it was heated to 75° C. for 48 h. LC-MS indicated the desired product. Dissolved in 5 mL of DMF and purified via prep HPLC (5%-95% CH3CN/H2O) to give 28.1 mg of N-{3-[2-(2,2-difluoro-ethyl)-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl]-benzyl}-3,4-dimethoxy-benzamide. MS, electrospray 510.4 (M+H).

Provenance & Evidence