Acetone → 2-(5-Bromo-3-fluoropyridin-2-yl)propan-2-ol

Temperature

-78 °C

To 2,5-dibromo-3-fluoropyridine in toluene at −78° C. was added n-butyllithium drop wise. The resulting solution was stirred at −78° C. for 1.5 hours. Then at −78° C., added acetone drop wise to the reaction mixture and continue to stir reaction at −78° C. for 2 hours at which point LC-MS and TLC indicated the reaction was complete. The reaction was warmed to 0° C. and quenched with saturated ammonium chloride solution (aq.) and then diluted with water (50 mL) and extracted with ethyl acetate (2×100 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to afford crude product. Gradient column chromatography on silica eluting with 0 to 30% EtOAc/hexanes gave the desired product (1.04 g).

1. stirringto stir
2. customreaction at −78° C. for 2 hours at which point LC-MS and TLC
3. temperatureThe reaction was warmed to 0° C.
4. customquenched with saturated ammonium chloride solution (aq.)
5. additiondiluted with water (50 mL)
6. extractionextracted with ethyl acetate (2×100 mL)
7. dry with materialThe organic layer was dried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customto afford crude product

ORD record

ord-5732a6fe1f844aeea5063cee2d63e99f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227971B2