[H-].[Na+].[CH2:3]1COCC1.[C:8]1([C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CI>ClCCl>[CH3:3][N:17]1[CH:18]=[C:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:15]=[CH:16]1.[CH3:3][N:15]1[C:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:18][N:17]=[CH:16]1To a slurry of sodium hydride, 60% in mineral oil (1.2 g, 31 mmol) in 100 mL anhyd. THF at 0° C. was added 4-phenylimidazole (4.00 g, 28 mmol) in small portions under nitrogen. Upon complete addition, the reaction was homogeneous and orange. After 10 min, methyl iodide (2.1 ml, 33 mmol) was added and the reaction was allowed to warm to ambient temperature. After 2 h, the reaction was quenched with 10 mL water and concentrated in vacuo. The resulting liquid was partitioned between water/brine and DCM. The aqueous layer was extracted with DCM (4×). The combined organic extracts were dried over anhyd sodium sulfate, filtered, and concentrated in vacuo to give an orange solid. This was dissolved in dichloromethane and purified by silica gel chromatography, 120 g, 60 min, 0-50% 90/10 DCM/MeOH in DCM, to give 1-methyl-4-phenyl-1H-imidazole and 1-methyl-5-phenyl-1H-imidazole as off-white solids.
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