Water → methyl (E)-3-(4-chloro-1-(2-chloro-4-(phenylethynyl)benzyl)-2-methylimidazol-5-yl)-2-propenate

Participants

Reaction Steps

To a mixture of methyl (E)-3-(4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazol-5-yl)-2-propenate (360 mg), dichlorobis(triphenylphosphine)palladium(II) (28 mg) and copper iodide (7.6 mg) was added a solution of phenylacetylene (326 mg) in diisopropylamine (20 ml) in a nitrogen atmosphere and the mixture was ref luxed under heating for 5 hr. The reaction mixture was allowed to cool. Water was added and the mixture was extracted twice with chloroform. The organic layers were combined, washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The resultant was filtrated under reduced pressure and concentrated to give a crude product. The product was applied to flash silica gel column chromatography (silica gel 10 g) to give methyl (E)-3-(4-chloro-1-(2-chloro-4-(phenylethynyl)benzyl)-2-methylimidazol-5-yl)-2-propenate as brown amorphous (331 mg) from the eluted fraction of hexane/ethyl acetate=5/1–1-1.

Provenance & Evidence