2-Pyridone → HCID 18779708, compound

HRID 1421700Notes

Reaction equation

HRID 1421700 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][C:12]([CH3:15])=[CH:11][N:10]=1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.[Cu]>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([N:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]2=[O:7])=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 88712-PyridoneHCID 11430Potassium CarbonateHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 18779708HCID 18779708, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Pyridinone (1.00 g, 10.5 mmol), 2-bromo-5-methylpyridine (1.81 g, 10.5 mmol), Copper (0.013 g, 0.20 mmol) and K2CO3 (1.60 g, 11.6 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2×) and the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc as eluent) to afford the title compound as a white solid.

Workup

  1. temperatureThe brown reaction mixture was cooled
  2. washwashed with saturated NaHCO3
  3. extractionThe aqueous layer was extracted with EtOAc (2×)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed (silica gel, EtOAc as eluent)

Sources & evidence

ORD record
ord-1b37b9d051244c248b4d8a7f9204eb51
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

Loading…