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

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Reaction Steps

To a solution of ethyl 3-{[5-(biphenyl-4-yl)-1-(biphenyl-4-ylmethyl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate (0.088 g, 0.140 mmol) and Pd(OH)2 (0.026 g, 0.036 mmol) in 1.5 mL of EtOAc and 0.75 mL of EtOH was added 1,4-cyclohexadiene (0.337 mL, 3.60 mmol). The resulting black suspension was microwaved at 130° C. for 2 h, and then filtered through a Celite™ pad eluting with 100% EtOAc. The resulting filtrate was then concentrated in vacuo. Purification of the resulting residue by reverse phase Gilson™ HPLC (30-100% MeCN/H2O) gave the title compound. LCMS: calculated for C27H24F2N2O3 462.49, observed m/e 462.9 (M+H)+484.9 (M+Na) (Rt 2.45/4 min).

Provenance & Evidence