Ethanol → HCID 21984597, compound

HRID 9195Notes

Reaction equation

HRID 9195 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[N:13]([O-])=O.[Na+].C(O)C.O>C(O)(=O)C.[Zn]>[Br:1][C:2]1[N:7]2[N:8]=[C:9]([O:11][CH3:12])[C:10]([NH2:13])=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 219846587-Bromo-2-methoxypyrazolo[1,5-a]pyridineHCID 23668193Sodium Nitrite

Product 1

HCID 21984597HCID 21984597, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

After dissolving 7-bromo-2-methoxypyrazolo[1,5-a]pyridine (1 g) in acetic acid (10 mL), an aqueous solution (5 mL) containing sodium nitrite (334 mg) was added and the mixture was stirred at room temperature for 20 minutes. After adding ethanol (60 mL) and water (30 mL) to the reaction mixture, zinc powder (1 g) was added and the mixture was heated and stirred at 60° C. for 30 minutes. The insoluble residue was filtered out, water was added, and extraction was performed with ethyl acetate. After washing the organic layer with brine, drying it over anhydrous magnesium sulfate and filtering it, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (750 mg) was obtained from the n-hexane:ethyl acetate (3:1) fraction as brown crystals.

Workup

  1. additionwas added
  2. additionwas added
  3. temperaturethe mixture was heated
  4. stirringstirred at 60° C. for 30 minutes
  5. filtrationThe insoluble residue was filtered out
  6. additionwater was added
  7. extractionextraction
  8. washAfter washing the organic layer with brine
  9. dry with materialdrying it over anhydrous magnesium sulfate
  10. filtrationfiltering it
  11. concentrationthe solvent was concentrated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-52c83a0963b84c5a9ed2f488112b8ecf
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Reaction notes

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