Potassium Carbonate → methyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetate

HRID 919291

Reaction equation

HRID 919291 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.Br[CH2:10][C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178515818HCID 178515818, compound

Product 1

HCID 28834262methyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromopyridin-2-ol (100 mg, 0.57 mmol), methyl 2-bromoacetate (168 mg, 1.1 mmol) and potassium carbonate (238 mg, 1.7 mmol) in acetone (5 mL) was stirred at 60° C. for 3 h. The solution was allowed to cool to room temperature, filtered and the filter cake was washed with acetone (5 mL×2). The filtrate was collected and concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography (PE: EA=15:1) to afford the title compound: LC/MS m/z=246.1 [M+H]+

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washthe filter cake was washed with acetone (5 mL×2)
  4. customThe filtrate was collected
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product, which
  7. customwas purified by silica gel column chromatography (PE: EA=15:1)

Sources & evidence

ORD record
ord-533fe365af6243879bca6a64e34b8f94
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Linked notes

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