Methyl Thioglycolate → HCID 59253215, compound

Participants

Reaction Steps

To a solution of 5-bromo-1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazole (Step D, 4.0 g, 12.5 mmol) in 1,4-dioxane (25 mL) were added N,N′-diisopropylethylamine (4.4 mL, 25 mmol), methyl mercaptoacetate (1.1 ml, 12.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (284 mg, 0.31 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (362 mg, 0.63 mmol). The mixture was stirred at reflux temperature for 24 h under nitrogen atmosphere. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 as eluent) to afford the title compound (4.75 g, quant.) as a pale yellow oil.

Provenance & Evidence