Water → 2-(2-Bromo-5-fluoro-pyridin-4-yl)-propane-1,2-diol

To a solution of 2-bromo-5-fluoro-4-isopropenyl-pyridine (17.1 g, 79 mmol) in acetone (50 mL) and H2O (100 mL) was added N-methylmorpholine oxide (10.51 g, 87 mmol) and OsO4 (4.97 mL, 4.02 g, 0.396 mmol). The biphasic mixture was stirred at rt for 17 h. The reaction mixture was quenched with sodium hydrosulfite (1.516 g, 8.71 mmol) in H2O (50 ml) and stirred at rt for 20 min. The reaction mixture was filtered through celite and the celite pad was washed three times with acetone. The combined filtrates were evaporated and the residue was taken up with EtOAc and 1N aq. NaOH soln. The phases were separated and the aq. phase was reextracted with EtOAc. The combined org. phases were dried over Na2SO4, filtered and concentrated to yield the title compound as a light purple solid. HPLC RtH4=0.60 min; ESIMS: 250, 252 [(M+H)+]; 1H NMR (400 MHz, DMSO-d6): δ 8.32 (d, 1H), 7.71 (d, 1H), 5.57 (s, 1H), 4.89 (t, 1H), 3.65-3.57 (m, 1H), 3.53-3.45 (m, 1H), 1.39 (s, 3H).

1. stirringstirred at rt for 20 min
2. filtrationThe reaction mixture was filtered through celite
3. washthe celite pad was washed three times with acetone
4. customThe combined filtrates were evaporated
5. customThe phases were separated
6. dry with materialphases were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-f7588d05f19241eeaf551347c2f7b1c4

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865712B2