Dimethyl Sulfoxide → 1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)-1H-imidazole

Participants

Reaction Steps

A mixture of 2-(4-fluorophenyl)-6-[(2-fluorophenyl)sulfonyl]naphthalene (110 mg, 0.29 mmol), imidazole (30 mg, 0.44 mmol), potassium carbonate (100 mg, 0.72 mmol) and dimethyl sulfoxide (1.5 mL) was reacted in a microwave at 150° C. for 20 minutes. The mixture was poured into water (100 mL) and extracted with ethyl acetate (2×50 mL). These extracts were washed with water and saturated brine then dried (MgSO4), filtered and solvent removed in vacuo. Purification by flash column chromatography eluting with 40% ethyl acetate/isohexane then 80% ethyl acetate/isohexane gave 1-(2-{[6-(4-fluorophenyl)-2-naphthyl]sulfonyl}phenyl)-1H-imidazole (104 mg, 84%). 1H NMR (500 MHz, CDCl3) δ 8.55 (1H, dd, J=1.7, 7.8 Hz), 7.96 (1H, s), 7.91 (1H, d, J=8.6 Hz), 7.89 (1H, s), 7.83 (1H, d, J=8.7 Hz), 7.80 (1H, dd, J=1.7, 8.5 Hz), 7.75-7.65 (4H, m), 7.42 (1H, dd, J=1.8, 8.6 Hz), 7.29 (1H, s), 7.23-7.17 (3H, m), 6.97 (1H, s), 6.75 (1H, s); m/z (ES+) 429 [MH+].

Provenance & Evidence