Imidazole → 5-(1H-Imidazol-2-yl)-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

Participants

Reaction Conditions

Reaction Steps

Imidazole (200 mg, 2.9 mmol) and MgO (60 mg, 2.9 mmol) were suspended in 0.5 ml dry dioxane and 2.5 ml dry DMF in a reaction bottle and stirred at room temperature for 5 minutes to form a homogeneous suspension. CuI (300 mg, 1.5 mmol), Pd(OAc)2 (18 mg, 0.0734 mmol), PPh3 (60 mg, 0.22 mmol) and 5-iodo-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (300 mg, 0.7335 mmol) were added to the above solution and reaction mixture were heated to 150° C. under microwave irradiation for 45 minutes. The reaction mixture was cooled, diluted with water, extracted with ethyl acetate, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give 165 mg of 5-(1H-Imidazol-2-yl)-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (65%), MS (M+H)=350.

Provenance & Evidence