Water → HCID 18332957, compound

Participants

Reaction Steps

2M Aqueous sodium carbonate solution (1.25 ml) was added to a suspension of 1-[3-(4-bromophenyl)propanoyl]-3-(N,N-dimethylamino)methyl-1,2,3,4-tetrahydroquinoline p-toluenesulfonate (400 mg) in toluene (10 ml) and ethanol (1.25 ml), which was stirred at room temperature for 10 minutes. 4-Methylbenzene boronic acid (123 mg) and tetrakis(triphenylphosphine)palladium (24 mg) were added to the reaction mixture, which was heated under reflux under an argon atmosphere for 14 hours. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: hexane/ethyl acetate=10/1 to 2/1), which was converted into its p-toluenesulfonate. The mixture was recrystallized from ethyl acetate to give the entitled compound (296 mg).

Provenance & Evidence