Methyl iodide → HCID 44553222, compound

Participants

Reaction Steps

4-{5-[(4-Chlorophenyl)thio]-2-phenyl-1H-imidazol-4-yl}benzonitrile (Example 1, 222 mg, 0.57 mmol) was dissolve in THF (6 mL), to which was added NaH (60% wt, 27.5 mg, 0.687 mmol) at 0° C. After stirring for 5 min, MeI (0.05 mL, 0.86 mmol) was added. The reaction was stirred at 0° C. for 2 h, and then quenched with aq NH4Cl to adjust the pH to 6-8. The product was extracted with EtOAc and the organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was subject to silica column chromatography (0-20% EtOAc in hexanes) to give the title compound as the major region isomer. 1H NMR (500 MHz, (CD3OD): 8.18 (d, 2H), 7.77 (m, 2H), 7.76 (d, 2H), 7.68 (m, 3H), 7.34 (d, 2H), 7.09 (d, 2H), 3.70 (s, 3H). LCMS: m/z 402 (M+H)+. The minor region isomer was the title compound of Example 3.

Provenance & Evidence