Isobutylene oxide → 4-Bromo-1-(2-hydroxy-2-methylpropyl)-2(1H)-pyridinone

HRID 406745Notes

Reaction equation

HRID 406745 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH3:9][C:10]1([CH3:13])[CH2:12][O:11]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:9][C:10]([OH:11])([CH3:13])[CH3:12])[C:4](=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 8171154-Bromo-2-hydroxypyridine

Product 1

HCID 596357304-Bromo-1-(2-hydroxy-2-methylpropyl)-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-1H-pyridin-2-one (0.25 g), 2,2-dimethyl-oxirane (0.26 mL), and potassium carbonate (0.40 g) in dimethylformamide (2.5 mL) was stirred under microwave irradiation at 120° C. for 30 min. After cooling to ambient temperature, the mixture was concentrated and purified by HPLC on reversed phase (acetonitrile/water) to afford the title compound. Yield: 0.34 g (96% of theory); Mass spectrum (ESI+): m/z=246/248 (Br) [m+H]+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture was concentrated
  3. custompurified by HPLC on reversed phase (acetonitrile/water)

Sources & evidence

ORD record
ord-f2b3801647474aebbf9c8f1434604737
Source dataset
uspto-grants-2014_06
Patent number
US08754076B2

Reaction notes

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