Tricyclohexylphosphine → HCID 44177595, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of compound 4-bromo-1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazole (224 mg, 0.430 mmol), cyclopropyl boronic acid (55 mg, 0.640 mmol), P(Cy)3 (23 mg, 0.082 mmol) and K3PO4.H2O (345 mg, 1.50 mmol) in 2.5 mL toluene and 0.15 mL H2O was added Pd(OAc)2 (10 mg, 0.044 mmol) in a 5 mL microwave tube. The tube was sealed and purged with an argon balloon for five minutes. The reaction was stirred for 24 h at 100° C. and cooled to room temperature. The reaction was diluted with ethyl acetate, and washed with saturated NH4Cl, brine, dried with MgSO4 and the solvent removed in vacuo. The residue was purified by column chromatography using hexanes:ethyl acetate as eluents and further purified by preparatory HPLC using water:TFA:acetonitrile as eluents to afford 4-cyclopropyl-1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazole (56 mgs, 27%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 8.13-8.12 (m, 1H), 8.03-8.00 (m, 1H), 7.91-7.88 (m, 1H), 7.83-7.80 (m, 1H), 7.77 (d, J=8.58 Hz, 2H), 7.74-7.69 (m, 1H), 7.64-7.62 (m, 2H), 7.46-7.44 (m, 1H), 7.41 (s, 1H), 7.25 (d, J=8.58 Hz, 2H), 3.28 (s, 3H), 1.93-1.87 (m, 1H), 0.86-0.82 (m, 2H), 0.76-0.72 (m, 2H); MS (ES): 483.0 [M+H]+.

Provenance & Evidence