Sodium Hydroxide → 5-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 751622Notes

Reaction equation

HRID 751622 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:17][C:11]2=[CH:12][N:13]=[C:14]([Br:16])[CH:15]=[C:10]2[CH:9]=1)=[O:7])C>C(O)C>[Br:16][C:14]1[CH:15]=[C:10]2[CH:9]=[C:8]([C:6]([OH:7])=[O:5])[NH:17][C:11]2=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50998338Ethyl 5-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 468357225-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide solution (1.1 mL, 2M, 2.23 mmol) was added to a solution of 5-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester (Preparation 26, 500 mg, 1.86 mmol) in ethanol (20 mL), and the reaction mixture heated under reflux for 1.5 h and then concentrated in vacuo. The residue was dissolved in water (15 mL) and acidified with acetic acid resulting in formation of a brown precipitate. The solid was collected by filtration and dried to give the title compound as a brown solid. δH (d6 DMSO): 7.08 (1H, s), 7.97 (1H, s), 8.60 (1H, s); m/z (ES+)=241 [M+H]+.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 1.5 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in water (15 mL)
  5. filtrationThe solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-4bfa0b8065884b1695b0db98d713e634
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

Loading…