Potassium Carbonate → HCID 178515692, compound

HRID 1515867Notes

Reaction equation

HRID 1515867 reaction equation
C([N:4]1[C:8]2=[N:9][C:10]([O:13]C(=O)C)=[CH:11][CH:12]=[C:7]2[CH:6]=[CH:5]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH:4]1[C:8]2=[N:9][C:10]([OH:13])=[CH:11][CH:12]=[C:7]2[CH:6]=[CH:5]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 247293951-Acetyl-1H-pyrrolo[2,3-b]pyridin-6-yl acetate

Product 1

HCID 178515692HCID 178515692, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of acetic acid 1-acetyl-1H-pyrrolo[2,3-b]pyridin-6-yl ester (4.0 g, 18.3 mmol) and potassium carbonate (10.45 g, 75.7 mmol) in methanol/water (50%, 260 mL) was stirred at room temperature for 12 h. The reaction mixture was concentrated to half its volume and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and evaporated. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 10% methanol/dichloromethane) afforded 1H-pyrrolo[2,3-b]pyridin-6-ol (1.52 g, 62%): LC/MS m/e calcd for C7H6N2O [M+H]+ 135.14, observed 135.0.

Workup

  1. concentrationThe reaction mixture was concentrated to half its volume
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-62dbae19759e45a593c7cdaad8ad42d7
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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