Water → 1H-Pyrrolo[2,3-b]pyridin-5-ol

HRID 2068029Notes

Reaction equation

HRID 2068029 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[N:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2.O>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:13](=[N:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 103078715-methoxy-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 220307221H-Pyrrolo[2,3-b]pyridin-5-olYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

Boron tribromide (0.506 μl, 5.35 mmol) in methylene chloride (1 ml) was added to a solution of 5-methoxy-7-azaindole (0.36 g, 2.43 mmol) in methylene chloride (25 ml) cooled at −30° C. The mixture was left to warm up to ambient temperature and was stirred overnight. The mixture was poured onto ice and water and the pH of the aqueous phase was adjusted to 6. The organic phase was separated and the aqueous phase was further extracted with ethyl acetate. The organic phases were combined, washed with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography eluting with increasingly polar mixtures of methylene chloride and methanol to give 5-hydroxy-7-azaindole (0.23 g, 71%).

Workup

  1. waitThe mixture was left
  2. temperatureto warm up to ambient temperature
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was further extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by column chromatography
  9. washeluting
  10. temperaturewith increasingly polar mixtures of methylene chloride and methanol

Sources & evidence

ORD record
ord-1f5e5cbfaf124659a52b75a98e86f936
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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