Hydrochloric Acid → 6-Tert-butoxy-4-(2-fluorophenyl)-2-isobutylquinoline-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Palladium acetate (0.015 g, 0.65 mmol) and racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.12 g, 0.19 mmol) were added to toluene (10 ml) under a nitrogen atmosphere and the mixture was stirred at 40° C. for 30 min. The reaction mixture was cooled to room temperature and 6-bromo-4-(2-fluorophenyl)-2-isobutylquinoline-3-carbonitrile (0.50 g, 1.30 mmol), tert-butanol (0.25 ml, 2.61 mmol) and sodium tert-butoxide (0.188 g, 1.96 mmol) were added, and the mixture was stirred under a nitrogen atmosphere at 90° C. for 1 hr. The reaction mixture was cooled and 0.1N hydrochloric acid (10 ml) was added and the mixture was stirred at room temperature for 30 min. Toluene (50 ml) was added to the reaction mixture. The organic layer was washed with water (10 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography and crystallized from n-hexane to give 6-tert-butoxy-4-(2-fluorophenyl)-2-isobutylquinoline-3-carbonitrile (0.40 g; yield 82%) as pale-yellow crystals.

Provenance & Evidence