Dimethylformamide → (2-Chloro-3-Fluoropyridin-4-Yl)Methanol

Temperature

0 °C

2-Chloro-3-fluoropyridine (1.51 mL, 14.9 mmol) was added under nitrogen atmosphere at −78° C. to a mixture of 2.0 M lithium diisopropylamide (in THF) (7.44 mL, 14.9 mmol) and THF (24 mL), and the mixture was stirred at 0° C. for 2 hours. DMF (11.4 mL, 149 mmol) was added to the mixture, and the obtained mixture was stirred at 0° C. for additional 2 hours. Sodium borohydride (731 mg, 19.3 mmol) was then added thereto, and the mixture was stirred at 0° C. for 1 hour. Water was then added to the reaction solution, which was then extracted with ethyl acetate. The solution was washed with 1N HCl, sodium hydrogen carbonate solution and saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The resultant residue was purified by silica gel column chromatography to yield the title compound (1.4 g, 58%).

1. stirringthe obtained mixture was stirred at 0° C. for additional 2 hours
2. stirringthe mixture was stirred at 0° C. for 1 hour
3. extractionwas then extracted with ethyl acetate
4. washThe solution was washed with 1N HCl, sodium hydrogen carbonate solution and saturated saline
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled away under reduced pressure
7. customThe resultant residue was purified by silica gel column chromatography

ORD record

ord-403a94e6048f4086a20208d92e63435a

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569378B2