Methyl iodide → HCID 58542022, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask is added 5-[2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-phenyl]-3H-[1,3,4]oxadiazol-2-one (100 mg, 0.242 mmol) in DMF (4 mL) at 0° C., followed by the addition of NaH (19 mg, 0.475 mmol). The reaction mixture is stirred at 0° C. for 10 minutes, followed by the addition of MeI (103 mg, 0.726 mmol). The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is quenched with saturated NH4Cl (10 mL) and extracted with EtOAc (20 mL). The organic layer is separated, washed with brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash chromatography with 0-5% MeOH/CH2Cl2 as the eluent to afford 5-[2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-phenyl]-3-methyl-3H-[1,3,4]oxadiazol-2-one (92 mg, 89%) as a solid. LCMS (ESMS): m/z 427.63, 429.67 (M++1).

Provenance & Evidence