Tetrahydrofuran → 4-(Bromomethyl)-2-(1H-pyrazol-1-YL)pyridine

Temperature

65 °C

To a stirred solution of (2-(1H-pyrazol-1-yl)pyridin-4-yl)methanol (175 mg, 1.00 mmol) in diethyl ether (5 mL), PBr3 (0.11 mL, 1.00 mmol) was added dropwise at 0° C. Then THF (5 mL) was added to the resulting white precipitate and the mixture was heated at 65° C. for 1 h. The mixture was cooled to rt, diluted with ethyl acetate (5 mL) and poured into saturated aqueous NaHCO3 solution (5 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield the title compound (165 mg, 70%). [LCMS RtE=1.33 min, [M+H]+=237.9/239.9].

1. temperatureThe mixture was cooled to rt
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with ethyl acetate (2×5 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-69bb823c750d4b289af34adcebfc2638

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530648B2