Sodium Hydroxide → 6-Methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1749810Notes

Reaction equation

HRID 1749810 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 712789696-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 114577166-Methyl-1H-pyrrolo[2,3-b]pyridineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The synthesis was performed with reference to the known literature (US 2006/0148801). A solution of 6-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine (0.17 g, 0.60 mmol) in ethanol (5.0 mL) was added with 5 N aqueous sodium hydroxide (1.0 mL), and the mixture was refluxed for 8 hours by heating. The solvent was evaporated under reduced pressure, the residue was extracted with chloroform, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (80:20→60:40)) to obtain 6-methyl-1H-pyrrolo[2,3-b]pyridine (0.071 g, 90%).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. temperatureby heating
  3. customThe solvent was evaporated under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washthe organic layer was washed successively with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (80:20→60:40))

Sources & evidence

ORD record
ord-56582753497e40c0beab555e87611594
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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