Dimethylformamide → 1-(2-Pyridyl)-5-(2-pyridyl)-3-bromo-1,2-dihydropyridin-2-one

HRID 229642Notes

Reaction equation

HRID 229642 reaction equation
CN(C)C=O.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:15]=[CH:14][C:13]1=[O:24].[Br:25]N1C(=O)CCC1=O>O>[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:15]=[C:14]([Br:25])[C:13]1=[O:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 223189481-(2-Pyridyl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one

Product 1

HCID 223190411-(2-Pyridyl)-5-(2-pyridyl)-3-bromo-1,2-dihydropyridin-2-oneYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 ml of a dimethylformamide solution containing 0.07 g of 1-(2-pyridyl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one was incorporated with 0.07 g of N-bromosuccinic acid imide, under stirring and ice-cooling. After stirring the mixture at room temperature for 2 hours, it was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (ethyl acetate/hexane=3:1), to give 0.05 g of the title compound as a pale brown powder.

Workup

  1. temperatureice-cooling
  2. stirringAfter stirring the mixture at room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane=3:1)

Sources & evidence

ORD record
ord-097aadcdb5cb48f2b852bc58476ec410
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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