Water → 1H-Pyrrolo[2,3-b]pyridin-5-ol

HRID 916366Notes

Reaction equation

HRID 916366 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-d328c6e5873e45d5a6b457bf4d47af34
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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