Hydrogen Peroxide → HCID 58042378, compound

To the crude 2-cyclopropyl-3-(1,1-difluoroethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 268, 412 mg, 1.27 mmol) was added methanol (20 mL), and the stirred solution cooled in an ice bath. To the solution was added hydrogen peroxide solution (35% in water) (0.15 mL, 1.52 mmol) over 2 minutes. The solution was allowed to warm slowly to room temperature over 18 hours. The reaction was quenched by addition of 1M aqueous sodium thiosulfate solution (50 mL), and rapidly stirred for 15 minutes. The organics were removed in vacuo, and brine (50 mL) was added. The aqueous was extracted into ethyl acetate (3×100 mL). The combined organics were dried over magnesium sulfate, filtered and the solvent removed to leave an orange oil. The oil was purified through a plug of silica, eluting with 1:1 ethyl acetate:heptane to provide the title compound a white solid (155 mg, 57%).

1. temperaturethe stirred solution cooled in an ice bath
2. customThe reaction was quenched by addition of 1M aqueous sodium thiosulfate solution (50 mL)
3. customThe organics were removed in vacuo, and brine (50 mL)
4. additionwas added
5. extractionThe aqueous was extracted into ethyl acetate (3×100 mL)
6. dry with materialThe combined organics were dried over magnesium sulfate
7. filtrationfiltered
8. customthe solvent removed
9. customto leave an orange oil
10. customThe oil was purified through a plug of silica
11. washeluting with 1:1 ethyl acetate

ORD record

ord-97cc65e9be20499c9fdf03312991a56b

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2