Water → Methyl 4-bromo-α-methyl-2-oxo-1(2H)-pyridinepropanoate

HRID 1187925Notes

Reaction equation

HRID 1187925 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.Br[C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:14][O:13][C:11](=[O:12])[CH:10]([CH3:16])[CH2:15][N:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]1=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 8171154-Bromo-2-hydroxypyridine

Product 1

HCID 59635795Methyl 4-bromo-α-methyl-2-oxo-1(2H)-pyridinepropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-bromo-1H-pyridin-2-one (0.50 g), methyl 2-bromoisobutyrate (0.45 mL), and potassium carbonate (0.68 g) in dimethylformamide (5 mL) was stirred at 60° C. for 3 h. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 70:30->50:50) to afford the title compound. Yield: 0.53 g (67% of theory); Mass spectrum (ESI+): m/z=274/276 (Br) [M+H]+. Additionally 2-(4-bromo-pyridin-2-yloxy)-2-methyl-propionic acid methyl ester was obtained {Yield: 0.15 g; Mass spectrum (ESI+): m/z=274/276 (Br) [M+H]+}

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 70:30->50:50)

Sources & evidence

ORD record
ord-a4792d79ae9e43b880aeb908da3288af
Source dataset
uspto-grants-2014_03
Patent number
US08673899B2

Reaction notes

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