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

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

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

filtrationfiltered
custompurified via preparative HPLC
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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434743B2

Reaction notes

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Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 60984Methyl bromoacetate

HCID 5995285-Bromo-2-hydroxypyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent