Methane → HCID 53875955, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 5-bromo-2-n-butyl-1-(2-chlorophenyl)methyl-1H-benzimidazole-7-carboxylate (600 mg, 1.38 mmol), tetrakis(triphenylphosphine)palladium(O) (50 mg), toluene (3 mL) and 2M sodium carbonate solution (1.5 mL) was treated with a solution of phenylboronic acid (200 mg, 1.64 mmol) in methanol (0.3 mL). The resulting mixture was vigorously stirred under an argon atmosphere and heated at 80° C. for 18 hours. The cooled reaction was diluted with methylene chloride, 2M sodium carbonate solution and a few drops of ammonium hydroxide solution. Some insolubles were filtered, the organic phase was separated, dried (magnesium sulfate) and concentrated to 0.55 g of crude product. TLC on silica with 4:1 hexane/ethyl acetate gave an Rf of 0.33 for the product; the starting material had an Rf of 0.43. The crude product was dissolved in methylene chloride, treated with activated charcoal and the filtrate was concentrated to a small volume and chilled. The separated off-white crystals were filtered to afford 0.41 g (68%) of methyl 2-n-butyl-1-(2-chlorophenyl)methyl-5-phenyl-1H-benzimidazole-7-carboxylate; mp 103°-105° C.

Provenance & Evidence