Trimethyl borate → (6-Fluoropyridin-3-yl)boronic acid

To a mixture of 5-bromo-2-fluoro-pyridine (1.71 g, 6.20 mmol) in dry ether (100 mL) was added n-BuLi (1.6 M in hexane, 41.4 mL, 0.0663 mol) at −78° C. After 30 minutes, trimethyl borate (8.2 mL, 0.0722 mol) was added to the above mixture and the reaction was warmed to room temperature and stirred overnight. The reaction was quenched with water and brine and acidified with 10% HCl until pH=8. The mixture was extracted with EtOAc, washed with 50% brine, dried over MgSO4, filtered, concentrated to give 5.1 g (60%) of the desired product. The crude product was used in the next step without further purification.

1. customThe reaction was quenched with water and brine
2. extractionThe mixture was extracted with EtOAc
3. washwashed with 50% brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-389d1e60916a419da651bd801fcdf7e1

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07320986B2