3-Bromopyridine → 3-Bromopyridine-4-carboxaldehyde

3-Bromopyridine (1.582 g) was dissolved in tetrahydrofuran (20 ml), followed by the addition of a 1.5M solution of lithium diisopropylamide/cyclohexane (7.3 ml) in nitrogen atmosphere at −70° C., and the resulting mixture was stirred for 5 min. Continuously, 4-formylmorpholine (3 ml) was added thereto and stirred for 20 min, followed by the further stirring at room temperature for 30 min. An aqueous solution of saturated ammonium chloride was added to the reaction mixture, and then it was extracted with ethyl acetate. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless solid (749 mg, yield; 40%).

1. stirringstirred for 20 min
2. stirringfurther stirring at room temperature for 30 min
3. extractionit was extracted with ethyl acetate
4. washThe resulting organic layer was washed with water
5. dry with materialdried (over MgSO4)
6. customevaporated
7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

ORD record

ord-929211ebbb214eb2af974b9c82e4f640

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06790844B2