Benzoic Acid → HCID 86623948, compound

A solution of 2-(5-bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (100 mg, 0.387 mmol) in DCM (3.0 mL) was cooled in an ice water bath and treated with mCPBA (100.3 mg, 0.581 mmol). After stirring at room temperature for 4 h, the mixture was cooled and additional mCPBA was added (66.7 mg, 1 eq.). After stirring 18 h at room temperature, another 0.3 eq of mCPBA was added (13.3 mg). Finally after 4 h, the reaction was quenched by addition of 38% aqueous sodium bisulfite (100 uL) and the mixture was dried over Na2SO4. After filtration, MP—CO3 (1.74 mmol) was added to scavenge the benzoic acid by-product. After 5 d (3 hours is sufficient), the mixture was filtered and the resin was rinsed with 10% MeOH in DCM. The product was concentrated in vacuo to afford 2-(5-bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide N-oxide (97.0 mg, 91.7%). MS: m/z 275 (M+H+).

1. temperaturethe mixture was cooled
2. stirringAfter stirring 18 h at room temperature
3. waitFinally after 4 h
4. customthe reaction was quenched by addition of 38% aqueous sodium bisulfite (100 uL)
5. dry with materialthe mixture was dried over Na2SO4
6. additionwas added
7. waitAfter 5 d (3 hours is sufficient)
8. filtrationthe mixture was filtered
9. washthe resin was rinsed with 10% MeOH in DCM
10. concentrationThe product was concentrated in vacuo

ORD record

ord-cefeb13f7ea14b7092ff3f6745eb75c7

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242280B2