p-Toluenesulfonic acid → HCID 44176495, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)-phenyl)-1H-imidazole-4-carbohydrazide (198 mg, 0.395 mmol) and triethyl orthoformate (1 mL, 6.01 mmol) in 1 mL xylenes was added a catalytic amount of p-toluenesulfonic acid. The reaction was heated at 130° C. for 12 h. The reaction was cooled and the mixture was absorbed onto silica and purified by column chromatography using hexanes:ethyl acetate as eluents to afford 2-(1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)-1,3,4-oxadiazole (96 mgs, 48%) as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 8.48 (s, 1H), 8.12 (s, 1H), 8.11-8.10 (m, 1H), 7.97-7.94 (m, 1H), 7.85-7.82 (m, 1H), 7.77-7.75 (m, 1H), 7.67 (t, J=7.83 Hz, 1H), 7.61-7.58 (m, 4H), 7.48-7.45 (m, 1H), 7.29-7.27 (m, 2H), 3.09 (s, 3H); MS (ES): 511.4 [M+H]+ and 533.0 [M+Na]+.

Provenance & Evidence