1,4-Cyclohexadiene → Ethyl 3-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclobutane carboxylate

Participants

Reaction Steps

To a solution of ethyl 3-{[5-(biphenyl-4-yl)-1-(biphenyl-4-ylmethyl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclobutanecarboxylate (0.160 g, 0,260 mmol) and Pd(OH)2 (0.048 g, 0.068 mmol) in 2.5 mL of EtOAc and 1.25 mL of EtOH was added 1,4-cyclohexadiene (0.630 mL, 6.70 mmol). The resulting black suspension was microwaved at 130° C. for 2 h. Then the reaction was filtered through a Celite™ pad, washed with 100% EtOAc, and the filtrate was concentrated in vacuo. Purification of the resulting residue by reverse phase Gilson™ HPLC (50-100% MeCN/H2O) afforded the title compound as a white solid. LCMS: calculated for C26H22F2N2O3 448.46, observed m/e 449.0 (M+H)+ (Rt 2.27/4 min).

Provenance & Evidence