Methyl Thioglycolate → HCID 59253215, compound

Participants

Reaction Steps

To a solution of 5-bromo-1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazole (Step D, 1.40 g, 4.36 mmol) in 1,4-dioxane (9 mL) were added N,N-diisopropylethylamine (1.52 mL, 8.72 mmol), methyl mercaptoacetate (0.39 ml, 4.36 mmol), tris(dibenzylideneacetone)dipalladium(0) (200 mg, 0.218 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (252 mg, 0.436 mmol). The mixture was heated to reflux for 21 h under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure to give a dark brown syrup. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1 as eluent) to afford the title compound (1.95 g, quant.) as an orange syrup.

Provenance & Evidence