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

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Reaction Steps

To a solution of ethyl 2-({[5-(biphenyl-4-yl)-1-(biphenyl-4-ylmethyl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}methyl)cyclopropanecarboxylate (0.270 g, 0.439 mmol) and Pd(OH)2 (0.080 g, 0.114 mmol) in 3.6 mL of EtOAc and 1.8 mL of EtOH was added 1,4-cyclohexadiene (1.06 mL, 11.3 mmol). The resulting black suspension was microwaved at 130° C. for 2 h, and then filtered through a Celite™ pad, and washed with 100% EtOAc. The resulting filtrate was concentrated. Purification of the resulting crude product by reverse phase Gilson™ HPLC (50-100% AcCN/H2O) afforded the desired product. LCMS: calculated for C26H22F2N2O3 448.46, observed m/e 448.9 (M+H)+ (Rt 2.37/4 min).

Provenance & Evidence