2-Bromopyridine → [1(2H),2'-Bipyridin]-2-one

HRID 547672Notes

Reaction equation

HRID 547672 reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].Br[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+].[I-]>O.CN(C)C=O>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7]

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 88712-PyridoneHCID 11430Potassium CarbonateHCID 30165Iodide Ion

Product 1

HCID 598976[1(2H),2'-Bipyridin]-2-oneYield 21.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

25 ml of a dimethylformamide solution containing 4.00 g of 2(1H)-pyridone and 8.00 g of 2-bromopyridine was incorporated with 3.80 g of potassium carbonate and 0.51 g of cupurous iodide, followed by stirring at 120° C. for 2 hours. After the mixture was returned to room temperature, water was added thereto. The mixture was extracted with ethyl acetate, and the ethyl acetate 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=1:1), to give 1.58 g of the title compound as a pale yellow wax.

Workup

  1. customwas returned to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe ethyl acetate layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane=1:1)

Sources & evidence

ORD record
ord-1b009ed38bf14a60a9a75b91ac6eff50
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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