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

HRID 2222432Notes

Reaction equation

HRID 2222432 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.[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 5360545SodiumHCID 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 hydroxyde (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-7dd2c36f16f94512b7b4b8c896631e44
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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