Trimethylazanium;chloride → 1-(6-Bromo-3-hydroxypyridin-2-YL)ethanone

To a suspension (30 mL) of aluminum chloride (3.96 g) in toluene was added trimethylammonium chloride (1.32 g), and the mixture was stirred under argon atmosphere at room temperature for 1 hr. A solution (30 mL) of 1-[3-(benzyloxy)-6-bromopyridin-2-yl]ethanone (2.81 g) synthesized above in toluene was added to the mixture, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous Rochelle salt solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-5% ethyl acetate/hexane) to give the title object compound (1.64 g, 83%) as a yellow solid.

1. additionwas added to the mixture
2. stirringthe mixture was stirred at room temperature for 3 hr
3. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous Rochelle salt solution
4. additionwas added to the residue
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (0-5% ethyl acetate/hexane)

ORD record

ord-a2661d90993c45eda2e624fbe304906a

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2