Ammonium Chloride → (5-Fluoro-pyridin-2-yl)-(8-nitro-quinolin-7-yl)-methanol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

n-BuLi (1.6M in hexane; 5.5 ml, 8.9 mmol) was added to anhydrous toluene (35 ml) at −78° C. under an N2 atmosphere followed by dropwise addition of a solution 2-bromo-5-fluoropyridine (1.56 g, 8.9 mmol) in anhydrous toluene (10 ml). The mixture was stirred at −78° C. for 45 min. The mixture was added to a solution of 8-nitroquinoline-7-carbaldehyde (Intermediate 204) (1 g, 5.0 mmol) in THF (50 ml) at −78° C. over 10 min. The mixture was stirred at −78° C. for a further 1 h. NH4Cl solution (10 ml) was added at −78° C. and the mixture was warmed to room temperature. The solvent was removed in vacuo. The residue was dissolved in DCM (50 ml) and the organic phase was washed with sat. NaHCO3 solution, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography DCM/MeOH (99:1) as the eluent to give the title compound (700 mg, 46%).

Herkunft & Nachweise