Ethyl bromoacetate → ethyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetate

HRID 1187943Notes

Reaction equation

HRID 1187943 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 28834261ethyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetateYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 5-bromopyridin-2(1H)-one (348 mg, 2.0 mmol) and K2CO3 (830 mg, 6.0 mmol) in DMF (15 mL) was added ethyl bromoacetate dropwise. The mixture was stirred at room temperature for 2 h, filtered, and the filtrate was concentrated in vacuo. The residue was purified by prep TLC (1:1 PE/EtOAc) to afford ethyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetate (300 mg, 57.7%). 1H NMR CDCl3: δ 7.41-7.26 (m, 2H), 6.53-6.5 (d, 1H), 4.59 (s, 2H), 4.28-4.21 (q, 2H), 1.32-1.23 (q, 3H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by prep TLC (1:1 PE/EtOAc)

Sources & evidence

ORD record
ord-f9050844e99342aba1edd8076c97270e
Source dataset
uspto-grants-2014_03
Patent number
US08673899B2

Reaction notes

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