Water → HCID 59635660, compound

HRID 1640852Notes

Reaction equation

HRID 1640852 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5]Br.[Br:10][C:11]1[CH:16]=[CH:15][NH:14][C:13](=[O:17])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][N:14]1[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][C:13]1=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8171154-Bromo-2-hydroxypyridineHCID 19604604methyl 3-bromo-2,2-dimethylpropanoate

Product 1

HCID 59635660HCID 59635660, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-Bromo-2,2-dimethyl-propionic acid methyl ester (0.75 g) was added to a mixture of 4-bromo-1H-pyridin-2-one (0.55 g) and potassium carbonate (0.75 g) in N,N-dimethylformamide (10 mL) at room temperature. The mixture was heated to 60° C. and stirred at this temperature overnight. After stirring at 80° C. for another 8 h, the mixture was cooled to room temperature and water was added. The resultant mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1) to afford the title compound; 3-(4-bromo-pyridin-2-yloxy)-2,2-dimethyl-propionic acid methyl ester (0.35 g) was also obtained from this reaction. Yield: 0.29 g (32% of theory); Mass spectrum (ESI+): m/z=288/300 (Br) [M+H]+.

Workup

  1. stirringAfter stirring at 80° C. for another 8 h
  2. temperaturethe mixture was cooled to room temperature
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-8e2ddbaa5caa42b3bbb07d2132c1e04e
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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