Potassium Carbonate → HCID 18797034, compound

Participants

Reaction Steps

2-(4-(4-Phenylbenzoylamino)butyl)-7-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydroisoquinoline (0.515 g, 0.97 mmol), (1-ethoxyvinyl)tributyltin (0.420 g, 1.16 mmol), lithium chloride (0.121 g, 2.85 mmol) and tetrakis-(triphenylphosphine)palladium (0) (0.057 g, 0.05 mmol) in 1,4-dioxane (15 ml) were heated at reflux under argon for 16 h. The cooled reaction mixture was treated with water (2.0 ml) and aqueous 5N hydrogen chloride (4 drops), then stirred at room temperature for 0.5 h. The resulting solution was poured onto saturated, aqueous potassium carbonate (20 ml) and the product was extracted with ethyl acetate (2×25 ml). The combined organic extracts were washed with brine (40 ml), dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica using 50-100% ethyl acetate--pentane gradient elution to afford the title compound as a colourless solid (0.210 g, 51%).

Provenance & Evidence