5-Bromo-2-(trifluoromethyl)pyridine → (8-Nitro-quinolin-7-yl)-(6-trifluoromethyl-pyridin-3-yl)-methanol

Temperatur

-78 °C

n-BuLi (1.6M in hexane; 2.77 ml, 4.43 mmol) was added dropwise to a solution of 5-bromo-2-(trifluoromethyl)pyridine (1 g, 4.42 mmol) in THF (5 ml) at −78° C. The mixture was stirred at −78° C. for 30 min before 8-nitroquinoline-7-carbaldehyde (Intermediate 204) (0.89 g, 4.42 mmol) in THF (10 ml) was added and the mixture was stirred at −78° C. for 10 min. The mixture was quenched with sat. NH4Cl (5 ml) at −78° C. and allowed to warm to room temperature. The resulting mixture was extracted with EtOAc (50 ml, ×2), the organic phase was washed with brine (20 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAc (50:50) as the eluent to give the title compound (350 mg, 23%).

1. additionwas added
2. customThe mixture was quenched with sat. NH4Cl (5 ml) at −78° C.
3. temperatureto warm to room temperature
4. extractionThe resulting mixture was extracted with EtOAc (50 ml, ×2)
5. washthe organic phase was washed with brine (20 ml)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe crude residue was purified by column chromatography with heptane/EtOAc (50:50) as the eluent

ORD-Eintrag

ord-854905fa7fb946788473ff451d664910

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09102688B2