1,3-Cyclohexadiene → 5-[4,6-Difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 5-[1-biphenyl-4-ylmethyl-4,6-difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid methyl ester (900 mg, 1.467 mmol) and Pearlman's catalyst (20% Pd(OH)2 on carbon) (180 mg) in EtOAc-EtOH (2:1, 7 mL) was treated with cyclohexadiene (2351 mg), and the resulting reaction mixture was heated under microwave at 130° C. for 10 min, and then at 130° C. for another 10 min. The cooled reaction mixture was filtered through a Celite pad (washed with 10% MeOH—CH2Cl2), and the filtrate was absorbed onto silica gel and purified by ISCO flash chromatography to give desired product as a white foam.

Provenance & Evidence