Water → 1H-Pyrrolo[2,3-b]pyridin-5-ol

HRID 2068011Notes

Reaction equation

HRID 2068011 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-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

Adding boron tribromide in methylene chloride to a solution of 5-methoxy-7-azaindole in methylene chloride cooled at about −30° C. Leaving the mixture to warm up to ambient temperature and stirring it for a period of time, for example overnight. Pouring the mixture onto ice and water and adjusting the pH of the aqueous phase to about 6. Separating the organic phase and further extracting the aqueous phase with ethyl acetate. Combining the organic phases washing them with brine, drying them, for example over magnesium sulphate, and then evaporating them. The residue may then be purified, for example by column chromatography eluting with increasingly polar mixtures of methylene chloride and methanol to give 5-hydroxy-7-azaindole.

Workup

  1. customLeaving the mixture
  2. temperatureto warm up to ambient temperature
  3. customfor example overnight
  4. customSeparating the organic phase
  5. extractionfurther extracting the aqueous phase with ethyl acetate
  6. washwashing them with brine
  7. customdrying them
  8. washeluting
  9. temperaturewith increasingly polar mixtures of methylene chloride and methanol

Sources & evidence

ORD record
ord-9cbece42967d449b8311a4a38f892e3e
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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