Ammonium Chloride → 1-[2-[(4S)-4-(tert-butyldimethyl-silyloxy)-1,2,3,4-tetrahydroquinolin-1-yl]-4-pyridyl]-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

Participants

Reaction Conditions

Reaction Steps

200 mL of a toluene solution containing 20.00 g of 1-(2-bromo-4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxy-naphthalene was sonicated under reduced pressure, then, 975 mg of palladium acetate, 1009 mg of tri-tert-butyl-phosphonium tetrafluoroborate, 13.72 g of (4S)-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydroquinoline and 6.26 g of sodium tert-butoxide were added to the mixture under room temperature, and after replacing the atmosphere with nitrogen, the mixture was stirred at 100° C. for 4 hours. After cooling the mixture by allowing to stand, 100 mL of a saturated aqueous ammonium chloride solution, 100 mL of water and 100 mL of ethyl acetate were added to the reaction mixture, and said mixture was filtered with Celite. Celite was washed with 100 mL of ethyl acetate, and the organic layer was separated. Said organic layer was washed with 100 g of 20% saline solution, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1 to 4:1) to obtain 22.31 g (Yield: 80%) of 1-[2-[(4S)-4-(tert-butyldimethyl-silyloxy)-1,2,3,4-tetrahydroquinolin-1-yl]-4-pyridyl]-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene.

Provenance & Evidence