Acetic Acid → 5-chloro-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

HRID 751604Notes

Reaction equation

HRID 751604 reaction equation
C([O:3][C:4]([C:6]1[NH:14][C:13]2[C:8](=[N:9][C:10]([Cl:15])=[CH:11][CH:12]=2)[CH:7]=1)=[O:5])C.[OH-].[Na+].C(O)(=O)C>C(O)C.ClCCl>[Cl:15][C:10]1[N:9]=[C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[NH:14][C:13]2=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 45480460Ethyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

Product 1

HCID 116655855-chloro-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester (Preparation 5, 151 mg, 0.67 mmol) in ethanol (10 mL) was added sodium hydroxide (0.35 mL, 2M) and the stirred solution was heated at 70° C. for 2 h. The reaction mixture was then allowed to cool to rt and left to stand for 16 h. The pH was adjusted to 4 by addition of glacial acetic acid, the solvents removed in vacuo to give a white solid, which was suspended in dichloromethane and filtered through a sinter, washing with additional dichloromethane. The filter cake was washed with ethyl acetate (3×30 mL) and dried to give the title compound as a white solid. δH (CD3OD): 6.97 (1H, s), 7.17 (1H, d, 8.35 Hz), 7.83 (1H, d, 8.35 Hz); m/z (ES+)=197 [M+H]+; RT=2.82 min.

Workup

  1. temperatureto cool to rt
  2. waitleft
  3. customthe solvents removed in vacuo
  4. customto give a white solid, which
  5. filtrationfiltered through a sinter
  6. washwashing with additional dichloromethane
  7. washThe filter cake was washed with ethyl acetate (3×30 mL)
  8. customdried

Sources & evidence

ORD record
ord-ad38af65c0e0432d996a5813dc97fd2e
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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