Sodium borohydride → (5-Bromopyridin-2-yl)methanol

The commercially available 5-bromopyridine-2-carbaldehyde (2.0 g, 10.8 mmol) was dissolved in methanol (60 mL) and solid sodium borohydride (407 mg, 10.8 mmol) was added at 20° C. The reaction was stirred 30 minutes then the solvent was removed and 25 mL of saturated ammonium chloride solution was added and the reaction was extracted with 200 mL EtOAc which was washed with water and brine, 30 mL each. The organic phase was dried over magnesium sulfate and filtered through a 2 cm silica gel pad. The clear filtrate was concentrated by rotary evaporation to give a white solid, 1.99 g which was used as is.

1. customthe solvent was removed
2. addition25 mL of saturated ammonium chloride solution was added
3. extractionthe reaction was extracted with 200 mL EtOAc which
4. washwas washed with water and brine, 30 mL each
5. dry with materialThe organic phase was dried over magnesium sulfate
6. filtrationfiltered through a 2 cm silica gel pad
7. concentrationThe clear filtrate was concentrated by rotary evaporation
8. customto give a white solid, 1.99 g which

ORD record

ord-491226cb7823448eb88c3a49d5e23d4d

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227971B2