Water → 6-(2-chloropyridin-4-yl)-7-(4-fluorophenyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 429210

Reaction equation

HRID 429210 reaction equation
[NH:1]([C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1)N.[Cl:9][C:10]1[CH:15]=[C:14]([C:16](=O)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:13]=[CH:12][N:11]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[Cl:9][C:10]1[CH:15]=[C:14]([C:16]2[NH:1][C:3]3=[N:4][CH:5]=[CH:6][N:7]=[C:8]3[C:17]=2[C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 14878232-HydrazinopyrazineHCID 229879691-(2-Chloropyridin-4-yl)-2-(4-fluorophenyl)ethanone

Product 1

HCID 229879776-(2-chloropyridin-4-yl)-7-(4-fluorophenyl)-5H-pyrrolo[2,3-b]pyrazineYield 26.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Hydrazinopyrazine (6.2 g, 57 mmol) and 1-(2-chloropyridin-4-yl)-2-(4-fluorophenyl)ethanone (14 g, 57 mmol) were suspended in benzene (250 ml) and p-toluenesulfonic acid monohydrate (0.68 g) was added. The reaction mixture was then refluxed with azeotropic removal of water via Dean Stark trap. After 2 h, the benzene was removed in vacuo and di-ethylene glycol was added. The reaction mixture was heated at reflux. After 2 h, the reaction mixture was poured into ether with vigorous stirring. Water was added and the product was extracted into ether. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Methanol was added and the solid was filtered off to give 6-(2-chloropyridin-4-yl)-7-(4-fluorophenyl)-5H-pyrrolo[2,3-b]pyrazine (4.9 g) as a solid.

Workup

  1. customthe benzene was removed in vacuo and di-ethylene glycol
  2. additionwas added
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux
  5. waitAfter 2 h
  6. additionthe reaction mixture was poured into ether with vigorous stirring
  7. additionWater was added
  8. extractionthe product was extracted into ether
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. additionMethanol was added
  13. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-64a62073fcdf4d2f9f53adaad240c925
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Linked notes

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