Hydrazine → 4-Methoxy-1H-pyrrolo(2,3-c)pyridine

HRID 987542Notes

Reaction equation

HRID 987542 reaction equation
Br[C:2]1[C:3]([O:12][CH3:13])=[C:4]2[C:8](=[C:9](Br)[N:10]=1)[NH:7][CH:6]=[CH:5]2.NN>CCO.[Pd]>[CH3:13][O:12][C:3]1[CH:2]=[N:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2

Participants

5

Reactant 2

HCID 9321HydrazineHCID 224762675,7-Dibromo-4-methoxy-6-azaindole

Product 1

HCID 224762374-Methoxy-1H-pyrrolo(2,3-c)pyridineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5,7-Dibromo-4-methoxy-6-azaindole 36 (680 mg, 2.22 mmol), 5% Pd/C (350 mg, 0.17 mmol) and hydrazine (2.5 mL, 80 mmol) in EtOH was heated at reflux for 1 h. The reaction mixture was allowed to cool to rt, filtered through celite and the filtrate concentrated. Aqueous NH4OH (11% in H2O, 45 mL) was added to the residue and the solution was extracted with CH2Cl2 (3×30 mL). The combined organics were dried (MgSO4), filtered and concentrated to yield 4-methoxy-6-azaindole 37 (290 mg, 1.95 mmol, 88%) as an orange solid.

Workup

  1. temperatureat reflux for 1 h
  2. filtrationfiltered through celite
  3. concentrationthe filtrate concentrated
  4. additionAqueous NH4OH (11% in H2O, 45 mL) was added to the residue
  5. extractionthe solution was extracted with CH2Cl2 (3×30 mL)
  6. dry with materialThe combined organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-936d3f1a1f804cb3b7a652cf16e150df
Source dataset
uspto-grants-2003_10
Patent number
US06632819B1

Reaction notes

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