Potassium Carbonate → HCID 18779778, compound

HRID 1421703Notes

Reaction equation

HRID 1421703 reaction equation
[Br:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CCOC(C)=O.[Cu]>[Br:1][C:2]1[C:3](=[O:9])[N:4]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 5642162-Bromo-5-methylpyridineHCID 178517588HCID 178517588, compound

Product 1

HCID 18779778HCID 18779778, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3,5,-Dibromo -2-pyridinol (1.47 g, 5.81 mmol), 2-bromo-5-methylpyridine (1.00 g, 5.81 mmol), copper (0.008 g, 0.116 mmol) and K2CO3 (0.883 g, 6.39 mmol) were heated at 180° C. for 18 hrs. The brown reaction mixture was cooled, diluted with EtOAc and stirred with saturated NaHCO3 for 1 hr. 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: CH2Cl2 10:90 to 30:70 gradient elution) to afford the title compound as a white solid.

Workup

  1. temperatureThe brown reaction mixture was cooled
  2. extractionThe aqueous layer was extracted with EtOAc (2×)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was chromatographed
  7. wash(silica gel, EtOAc: CH2Cl2 10:90 to 30:70 gradient elution)

Sources & evidence

ORD record
ord-bf10bd36c553409b8f0ed43754e7d2a9
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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