Sodium hydride → 5-Bromo-2-(cyclopropylmethoxy)pyridine

To a solution of cyclopropylmethanol (0.890 mL, 11.0 mmol) in DMF (30 mL) was added sodium hydride (oil, 60%, 440 mg, 11.0 mmol), and the mixture was stirred at room temperature for 10 min. To this solution was added 2,5-dibromopyridine (2.00 g, 8.46 mmol) and the mixture was stirred at 70° C. for 1 hr. The reaction was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=49:1 to 17:3) to give the title compound (1.88 g, yield 97%) as an oil.

1. stirringthe mixture was stirred at 70° C. for 1 hr
2. customThe reaction was quenched with water
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed twice with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=49:1 to 17:3)

ORD record

ord-f7c97418b04d4972961acc0e3691b967

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501804B2