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

HRID 562846Notes

Reaction equation

HRID 562846 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-c01547fc4f53452b99a6c617a41cfccc
Source dataset
uspto-grants-2011_11
Patent number
US08067434B2

Reaction notes

Loading…