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

HRID 58048

Reaction equation

HRID 58048 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([O:13][CH3:14])=[O:12].C([O-])([O-])=O.[K+].[K+]>CS(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 5995285-Bromo-2-hydroxypyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To solution of 5-bromopyridin-2(1H)-one (2.5 g, 14.37 mmol) and methyl 2-bromoacetate (2.418 g, 15.81 mmol) in DMSO (12 mL) was added K2CO3 (2.383 g, 17.24 mmol). The mixture was stirred at 60° C. for 4 hours, filtered, and purified via preparative HPLC, eluting with a gradient of 10-90% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) to give the title compound.

Workup

  1. filtrationfiltered
  2. custompurified via preparative HPLC
  3. washeluting with a gradient of 10-90% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA)

Sources & evidence

ORD record
ord-8a9a13226ab74f98ba60f664d65d6a8f
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Linked notes

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