Water → ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]acrylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl trifluoromethanesulfonate (1.5 g, 2.8 mmol) in N,N-dimethylformamide (10 ml) were added dichlorobistriphenylphosphine palladium (0.021 g, 0.030 mmol), triethylamine (4.2 ml, 30 mmol) and ethyl acrylate (0.65 ml, 6.0 mmol) and the mixture was stirred at 70° C. for 6 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]acrylate (0.87 g, yield 62%) as pale-yellow crystals.

Provenance & Evidence