Trifluoromethanesulfonic anhydride → HCID 18675884, compound

Participants

Reaction Conditions

Reaction Steps

1.5 g (0.0103 mol) of 7-hydroxyisoquinoline and 5.3 ml of pyridine are cooled to 0° C. 1.86 ml of triflic anhydride are added dropwise thereto. The mixture is stirred for 1 hour at 0° C. and then for 2 hours at room temperature. The resulting mixture is poured into a water/ice mixture and extracted with ethyl acetate, the organic phase is dried and the solvent is evaporated off under reduced pressure. The crude product is purified by chromatography on a column of silica gel, eluting with a 7/3 cyclohexane/ethyl acetate mixture. 7-Hydroxyisoquinoline trifluoromethanesulphonate is obtained in the form of an oil. 1.65 g of this product are mixed with 27.5 ml of anhydrous dimethylformamide, 41 mg of palladium acetate, 1.65 ml of anhydrous triethylamine and 1.38 g of N,N-diethylethanolamine vinyl ether, under argon. This mixture is heated at 80° C. for 36 hours. The resulting mixture is poured into a water/ethyl acetate mixture, the two phases are separated, the organic phase is washed with water and dried, and the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a column of silica gel, eluting with a 9/1 ethyl acetate/methanol mixture. 2-[2-(7-Isoquinolyl(ethenyl)oxy)]-N,N-diethyl-1-ethanamine is obtained. 1.5 g of this product are treated with 130 ml of water and 13 ml of 96% sulphuric acid. This mixture is heated for 4.5 hours at 60° C. and poured into ice, saturated aqueous NaHCO3 solution is added thereto and the mixture is extracted with ethyl acetate. The organic phase is dried and the solvent is evaporated off under reduced pressure. The title compound is obtained.

Provenance & Evidence