Hydrochloric Acid → 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid

HRID 1785584Notes

Reaction equation

HRID 1785584 reaction equation
C(C1[CH:4]=[C:5]2[C:9](=[N:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#N.Cl.[C:13]([O:16]CC)(=[O:15])[CH3:14]>C(O)C.[OH-].[K+]>[NH:8]1[C:9]2[C:5](=[CH:4][C:14]([C:13]([OH:16])=[O:15])=[CH:11][N:10]=2)[CH:6]=[CH:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 117883551H-Pyrrolo[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 219070181H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-cyano-7-azaindole XXX (50 mg, 0.35 mmol) in ethanol (10 ml), 10% aqueous potassium hydroxide (15 ml) was added. The reaction was heated at 90° C. for two days after which the reaction was allowed to cool to room temperature. The pH was adjusted to 6 with 10% HCl and diluted with ethyl acetate (100 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (4×, 75 ml). The organic layers were combined and washed once with brine (100 ml) before drying over sodium sulfate. The organic layer was evaporated under reduced pressure to yield the titled product as an off-white solid. (52 mg, M−1, 161.2)

Workup

  1. temperatureto cool to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (4×, 75 ml)
  4. washwashed once with brine (100 ml)
  5. dry with materialbefore drying over sodium sulfate
  6. customThe organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5ebf79b70122467190ee81021dc71ef2
Source dataset
uspto-grants-2009_03
Patent number
US07504509B2

Reaction notes

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