Toluene → HCID 22998665, compound

Participants

Reaction Steps

A mixture of (+)-6-(2-bromopyridin-5-yl)methoxy-2-[2-(N,N-dimethylamino)ethyl]tetralin dihydrochloride (0.2 g), toluene (8 ml), ethanol (1 ml), 2M aqueous sodium carbonate (1 ml) was stirred at room temperature for 10 min. 4-methoxyphenylboric acid (89 mg), and tetrakis(triphenylphosphine)palladium (27 mg) was added and the reaction mixture was heated under reflux under argon for 15 hr and cooled. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:4) and then converted into its dihydrochloride, which was recrystallized from ethanol-ethyl acetate to obtain the titled compound (176 mg).

Provenance & Evidence