(Dimethyl sulfide)trihydroboron → 5-Bromo-1-(1-hydroxypropan-2-yl)pyridin-2(1H)-one

To a solution of 2-(5-bromo-2-oxopyridin-1(2H)-yl)propanoic acid (3.36 g, 13.7 mmol) in 50 mL of THF was added borane-dimethyl sulfide (3.89 ml, 41.0 mmol) via a syringe. The reaction was stirred at rt for 16 hours and was quenched with 10 mL of 1N HCl. The mixture was extracted with 70 mL of EtOAc twice. The combined organic phases were washed with brine and dried over Na2SO4. The solution was concentrated in vacuo to give a light yellow oil (2.50 g, 78.9% yield) which was used in the next step without further purification. MS (ESI pos. ion) m/z (MH+): 231.9. Calc'd Exact Mass for C8H10BrNO2: 230.99.

1. customwas quenched with 10 mL of 1N HCl
2. extractionThe mixture was extracted with 70 mL of EtOAc twice
3. washThe combined organic phases were washed with brine
4. dry with materialdried over Na2SO4
5. concentrationThe solution was concentrated in vacuo

ORD record

ord-201e2f5540d24cb799dffa66fa7f1917

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314087B2