Triethylamine → HCID 86758146, compound

Participants

Reaction Conditions

Reaction Steps

0.041 g of tetrakis(triphenylphosphine)palladium and 0.070 g of cuprous iodide were added, at a temperature in the region of 20° C. and under an inert atmosphere, to a stirred solution of 0.7 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)piperidine-3-carboxylate in 14 cm3 of acetonitrile. 0.32 cm3 of 1-fluoro-2-iodobenzene and 0.51 cm3 of triethylamine were subsequently added. The mixture was stirred at a temperature in the region of 20° C. for 20 hours. The reaction mixture was filtered and the cake was washed with 3 times 10 cm3 of acetonitrile. The combined filtrates were taken up with stirring in a mixture of 100 cm3 of dichloromethane and 100 cm3 of water. The organic phase was separated by settling, washed with 3 times 50 cm3 of a saturated sodium chloride solution, dried over magnesium sulfate, and then, after filtration, concentrated under reduced pressure (2 kPa) at a temperature in the region of 35° C. The residue obtained was purified by chromatography under argon pressure (50 kPa) on a column of silica gel (particle size 40-63 μm; diameter 4 cm; height 14 cm), elution was carried out with ethyl acetate, and 2-cm3 fractions were collected. Fractions 33 to 160 were combined and then evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C. 0.56 g of methyl (3R,4R)-4-(3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(2-fluorophenyl)prop-2-ynyl]piperidine-3-carboxylate was obtained in the form of an oil with a light brown color.

Provenance & Evidence