Dimethyl Sulfoxide → HCID 59239988, compound

Participants

Reaction Steps

To a −78° C. solution of oxalyl chloride (0.20 mL, 2.33 mmol) in 5 mL dichloromethane was added DMSO dropwise followed by (1-(3-chloro-3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-chlorophenyl)-1H-imidazol-4-yl)methanol (735 mg, 1.55 mmol) in 5 mL of dichloromethane. Triethylamine (1.3 mL, 9.30 mmol) was then added at −78° C. and the reaction was stirred 12 h and warmed to room temperature. The reaction was diluted with 50 mL ethyl acetate, washed with water 1×50 mL, brine, and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by column chromatography using hexanes:ethyl acetate as eluents to afford 1-(3-chloro-3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-chlorophenyl)-1H-imidazole-4-carbaldehyde (338 mgs, 47%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 9.90 (s, 1H), 8.56 (s, 1H), 8.22-8.21 (m, 1H), 8.12-8.09 (m, 2H), 7.97-7.94 (m, 1H), 7.84 (dd, J=8.33 Hz, J=2.04 Hz, 1H), 7.75 (t, J=7.82 Hz, 1H), 7.67-7.65 (m, 1H), 7.58-7.56 (m, 1H), 7.50-7.43 (m, 2H), 7.40-7.36 (m, 1H), 3.30 (s, 3H); MS (ES) 471.0 [M+H]+.

Provenance & Evidence