1H-Pyrrolo(2,3-b)pyridine → HCID 178526243, compound

HRID 491648Notes

Reaction equation

HRID 491648 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([O-])(O)=[O:11].[Na+].OOS([O-])=O.[K+]>CO.O>[NH:1]1[C:5]2=[N+:6]([O-:11])[CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 178526243HCID 178526243, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a suspension of 1H-pyrrolo[2,3-b]pyridine (20.0 g) and NaHCO3 (90 g) in 1:1 MeOH/H2O (1000 mL) was added Oxone® (212 g) in portions during a 40 min period. The mixture was stirred at RT for 5 h. The solid was removed by filtration and the filtrate was concentrated to dryness. The solid residue was washed several times with CH2Cl2/MeOH 90/10 (500 mL). The combined organic solutions were concentrated under vacuum. The resulting crystalline solid was dissolved in CH2Cl2 (1 L). The organic solution was dried over MgSO4 and the solvent was removed under vacuum. The crude material was purified on Silica gel using a CH2Cl2/EtOAc gradient (100/0 to 0/100) to afford 1H-pyrrolo[2,3-b]pyridine 7-oxide.

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. washThe solid residue was washed several times with CH2Cl2/MeOH 90/10 (500 mL)
  4. concentrationThe combined organic solutions were concentrated under vacuum
  5. dissolutionThe resulting crystalline solid was dissolved in CH2Cl2 (1 L)
  6. dry with materialThe organic solution was dried over MgSO4
  7. customthe solvent was removed under vacuum
  8. customThe crude material was purified on Silica gel using a CH2Cl2/EtOAc gradient (100/0 to 0/100)

Sources & evidence

ORD record
ord-75560efe255a4b95b2f1e10f16dedadd
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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