Water → HCID 178419413, compound

To a solution of pyrazole benzyl carbamate (115.0 mg, 0.38 mmol), prepared in step A, in 6 mL of CH2Cl2 at room temperature was added solid potassium carbonate in one portion. A solution of bromine was added dropwise to the stirred mixture. After 6 h, 30 mL of H2O was added, and the mixture was extracted with CH2Cl2 (30 mL×3). The combined organic extracts were washed with a 10% Na2S2O3 aqueous solution (20 mL), a saturated NaHCO3 aqueous solution (20 mL) and brine (20 mL), and dried with Na2SO4. Evaporation of solvent gave a slightly yellow oil, which was purified by preparative TLC (CH2Cl2-MeOH=20:1). The silica was extracted with CH2Cl2 and methanol, the extracts were filtered and concentrated under reduced pressure to afford an oil, which was further dried on high vacuum, yielding 134.2 mg (93%) of the bromo-pyrazole benzyl carbamate (MH+=381).

1. extractionthe mixture was extracted with CH2Cl2 (30 mL×3)
2. washThe combined organic extracts were washed with a 10% Na2S2O3 aqueous solution (20 mL)
3. dry with materiala saturated NaHCO3 aqueous solution (20 mL) and brine (20 mL), and dried with Na2SO4
4. customEvaporation of solvent
5. customgave a slightly yellow oil, which
6. customwas purified by preparative TLC (CH2Cl2-MeOH=20:1)
7. extractionThe silica was extracted with CH2Cl2 and methanol
8. filtrationthe extracts were filtered
9. concentrationconcentrated under reduced pressure
10. customto afford an oil, which
11. customwas further dried on high vacuum

ORD record

ord-6121a0a5c1ed4d23abc86f8e772ec64f

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06903131B2