Sodium hydride → 3-Bromo-4-(cyclopropylmethoxy)pyridine

To a solution of 3-bromo-4-chloropyridine (CAN 36953-42-1, 5 g, 26.0 mmol) in dry DMF (60 ml) under an argon atmosphere at room temperature was added cyclopropylmethanol (CAN 2516-33-8, 1.97 g, 27.3 mmol) and sodium hydride 60% (1.09 g, 27.3 mmol) by portions. The resulting reaction was stirred at room temperature until gas evolution stopped. The reaction mixture was then stirred at 100° C. for 3 h. The reaction was cooled down to room temperature, quenched by addition of water and the reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate, extracted with 1.0M aqueous solution sodium bicarbonate, organic phase dried over sodium sulfate and evaporated down to dryness. The crude was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the titled compound (5.8 gr, 98%) as a light yellow oil. MS (ESI, m/z): 228.1 (M+H+).

1. customThe resulting reaction
2. stirringThe reaction mixture was then stirred at 100° C. for 3 h
3. temperatureThe reaction was cooled down to room temperature
4. customquenched by addition of water
5. concentrationthe reaction mixture was concentrated in vacuo
6. dissolutionThe residue was dissolved in ethylacetate
7. extractionextracted with 1.0M aqueous solution sodium bicarbonate, organic phase
8. dry with materialdried over sodium sulfate
9. customevaporated down to dryness
10. customThe crude was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient

ORD record

ord-13780df408ab4ba09bbbad4c4ee52eb6

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409866B2