1,2-Dimethoxyethane → 2-(2-Furanyl)-5-(4-pyridinyl)pyrazine

HRID 352780Notes

Reaction equation

HRID 352780 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][N:3]=1.[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(COC)OC.[F-].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[O:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:5]1[CH:4]=[N:3][C:2]([C:16]2[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=2)=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 2734379(Pyridin-4-yl)boronic acidHCID 127614162-Chloro-5-(furan-2-yl)pyrazine

Product 1

HCID 227104122-(2-Furanyl)-5-(4-pyridinyl)pyrazineYield 58%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

At room temperature, 2-chloro-5-(furan-2-yl)pyrazine (N. Sato, J. Heterocyclic Chem., 19, 407(1982)) (1.00 g) and (pyridin-4-yl)boronic acid (1.09 g) were suspended in a mixed solvent of dimethoxyethane (50 ml) and methanol (50 ml), followed by the successive addition of tetrakis(triphenylphosphine)palladium (O) (640 mg) and cesium fluoride (5.55 g). The resulting mixture was heated under reflux for 16 hours. After cooling, the reaction mixture was concentrated. Dichloromethane and water were added to the concentrate to separate the organic layer. The organic layer was dried over anhydrous sodium sulfate, treated with activated carbon and filtered through Celite. After the filtrate was concentrated to about 5 ml, petroleum ether (50 ml) was added to the concentrate. Yellow crystalline powder thus precipitated was collected by filtration and dried, whereby the title compound (716 mg, 58%) was obtained.

Workup

  1. customAt room temperature
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 16 hours
  4. temperatureAfter cooling
  5. concentrationthe reaction mixture was concentrated
  6. additionDichloromethane and water were added to the
  7. concentrationconcentrate
  8. customto separate the organic layer
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. additiontreated with activated carbon
  11. filtrationfiltered through Celite
  12. concentrationAfter the filtrate was concentrated to about 5 ml, petroleum ether (50 ml)
  13. additionwas added to the concentrate
  14. customYellow crystalline powder thus precipitated
  15. filtrationwas collected by filtration
  16. customdried

Sources & evidence

ORD record
ord-d8aee96db22d4475a41db200780e5915
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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