Potassium Carbonate → HCID 22254317, compound

HRID 379070Notes

Reaction equation

HRID 379070 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.[Cu]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5642162-Bromo-5-methylpyridineHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 22254317HCID 22254317, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloro-2-pyridinol (2.26 g, 17.4 mmol), 2-bromo-5-methylpyridine (3.00 g, 17.4 mmol), copper (0.022 g, 0.35 mmol) and K2CO3 (2.66 g, 19.2 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: CH2Cl2 20:80 to 50:50 gradient elution) 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
  8. wash(silica gel, EtOAc: CH2Cl2 20:80 to 50:50 gradient elution)

Sources & evidence

ORD record
ord-1e20f7c579d24afc9eaded43a6f2462c
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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