Water → 5-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 2180155Notes

Reaction equation

HRID 2180155 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([CH3:12])[N:9](S(C3C=CC=CC=3)(=O)=O)[C:6]2=[N:7][CH:8]=1.[OH-].[Na+].O>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([CH3:12])[NH:9][C:6]2=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 222736535-methoxy-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 222736705-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-methoxy-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (950 mg, 3.14 mmol) and 40% aqueous sodium hydroxide (106 ml) in methanol (160 ml) was heated at reflux for 30 minutes. After cooling, the mixture was poured onto cooled water and extracted with ethyl acetate. The organic layer was separated, washed with water, brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1/1). The fractions containing the expected product were combined and evaporated to give 5-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine (462 mg, 91%).

Workup

  1. temperatureat reflux for 30 minutes
  2. temperatureAfter cooling
  3. additionthe mixture was poured
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography
  11. washeluting with ethyl acetate/petroleum ether (1/1)
  12. additionThe fractions containing the expected product
  13. customevaporated

Sources & evidence

ORD record
ord-54bc08efda3c475c90e139938210c896
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

Loading…