Boron tribromide → 1H-Pyrrolo[2,3-b]pyridin-5-ol

HRID 1024204Notes

Reaction equation

HRID 1024204 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>O1CCCC1.C(OCC)(=O)C.O>[NH:9]1[C:6]2=[N:7][CH:8]=[C:3]([OH:2])[CH:4]=[C:5]2[CH:11]=[CH:10]1

Participants

6

Reactant 2

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

Product 1

HCID 220307221H-Pyrrolo[2,3-b]pyridin-5-olYield 44.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-methoxy-1H-pyrrolo[2,3-b]pyridine (81, 0.5 g, 3 mmol) in tetrahydrofuran (20 mL) was added boron tribromide (1.5 g, 6.0 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature, then stirred at room temperature for 3 hours. The reaction mixture was quenched by methanol. After repeated addition of methanol and removal of solvent, the concentrated reaction mixture was dissolved in ethyl acetate and water. The organic layer was collected, washed with brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as an off-white solid (82, 0.18 g, 40%).

Workup

  1. customThe reaction mixture was quenched by methanol
  2. additionaddition of methanol and removal of solvent
  3. customthe concentrated reaction mixture
  4. customThe organic layer was collected
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of solvent
  8. customthe residue was purified by silica gel column chromatography
  9. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-f4bef01ed99147e0941d7531a058b9e8
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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