Hydrogen Peroxide → HCID 57418748, compound

Temperature

0 °C

1-Allyl-5-bromo-1H-indazole (1s) (0.50 g, 2.1 mmol) was dissolved in 2 mL THF and cooled to 0° C. A solution of 9-BBN in THF (0.5 M solution, 8.9 mL, 4.4 mmol) was then added slowly via syringe under nitrogen and stirring. The reaction was warmed to room temperature over 6.5 hours. Then, a solution of aqueous H2O2 (30% wt. solution; 1.4 mL) in 1 N NaOH (14 mL, 14 mmol) was added slowly to the solution. The reaction was stirred at room temperature overnight, resulting in the formation of a white precipitate. The reaction was diluted with H2O and Et2O. The layers were separated and the organic phase was washed with brine. The aqueous phases were extracted once with Et2O. The organic phases were combined, dried (MgSO4), filtered, and concentrated in vacuo. The crude material (2s) was carried on to the next step without characterization.

1. temperatureThe reaction was warmed to room temperature over 6.5 hours
2. stirringThe reaction was stirred at room temperature overnight
3. customresulting in the formation of a white precipitate
4. customThe layers were separated
5. washthe organic phase was washed with brine
6. extractionThe aqueous phases were extracted once with Et2O
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-1d0d7e62b6af439e87b98e8c22264bc9

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07799782B2