Sodium Hydroxide → 1H-Pyrrolo[2,3-b]pyridin-5-ol

HRID 1791703Notes

Reaction equation

HRID 1791703 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.B(Br)(Br)Br.[OH-].[Na+]>ClCCl.O>[OH:2][C:3]1[CH:4]=[C:5]2[CH:11]=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 103078715-methoxy-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 220307221H-Pyrrolo[2,3-b]pyridin-5-olYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 5-methoxy-1H-pyrrolo[2,3-b]pyridine (210 mg, 1.42 mmol), (Heterocycles 50, (2), 1065–1080, (1999)), in dichloromethane (10 ml) was stirred in an inert atmosphere, a 1.0M solution of boron tribromide in dichloromethane (4.3 ml, 4.3 mmol) added dropwise and the mixture stirred at ambient temperature overnight. The reaction mixture was taken to pH6 by the dropwise addition of 5N aqueous sodium hydroxide and further diluted with water. The aqueous solution was extracted several times with ethyl acetate, the extracts combined, washed with water followed by brine and dried over magnesium sulphate. The ethyl acetate solvent was removed ‘in vacuo’ and the residue purified by column chromatography, eluting with dichloromethane/methanol (95/5), to give a white solid. The solid was triturated with ether, filtered and dried to give 5-hydroxy-1H-pyrrolo[2,3-b]pyridine (108 mg, 57%).

Workup

  1. stirringthe mixture stirred at ambient temperature overnight
  2. extractionThe aqueous solution was extracted several times with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customThe ethyl acetate solvent was removed ‘in vacuo’ and the residue
  6. custompurified by column chromatography
  7. washeluting with dichloromethane/methanol (95/5)
  8. customto give a white solid
  9. customThe solid was triturated with ether
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-d1fd4ad30bad489e975d720d33a26162
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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