87034-78-4

2770-01-6

74-88-4

50432-68-3

87034-78-4

NaH (78 mg, 1.95 mmol, 60% oil dispersion) was added to a solution of 4-chloroimidazo[4,5-C]pyridine (100 mg, 0.65 mmol) in DMF (3 mL) at 0 °C. The mixture was stirred at 0 °C for 40 min under nitrogen protection. Subsequently, iodomethane (277 mg, 1.95 mmol) was added at 0 °C. The reaction mixture was continued to be stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc (20 mL x 3). The organic layers were combined, dried with magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by preparative HPLC to afford 4-chloro-1-methyl-1H-imidazo[4,5-c]pyridine (40.3 mg, yellow oil) and 4-chloro-3-methyl-3H-imidazo[4,5-c]pyridine (41.0 mg, yellow oil).LRMS (m/z): [M + H]+ Calculated Values 168.2, 170.2; measured values 168.0, 170.2.