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

HRID 2356858Notes

Reaction equation

HRID 2356858 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-4031db086890492abecbcf34e363eb5a
Source dataset
uspto-grants-2010_07
Patent number
US07759367B2

Reaction notes

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