Hydrochloric Acid → 1-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

HRID 1766158Notes

Reaction equation

HRID 1766158 reaction equation
[OH-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[C:11]([C:18]([O:20]C)=[O:19])=[CH:10]1.Cl>O1CCCC1>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[C:11]([C:18]([OH:20])=[O:19])=[CH:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21110085methyl 1-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 211100571-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.6 cm3 of 10N sodium hydroxide solution were added to methyl 1-(pyridine-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate in 15 cm3 of tetrahydrofuran. After stirring at reflux of the solvent for 200 h, the reaction mixture was acidified with 2 cm3 of 10N hydrochloric acid and then concentrated to dryness under reduced pressure (2.7 kPa) to give 1-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid in the form of a brown powder, characterized by LC/MS (m/z 240 [MH]+), which was used directly in the following stage.

Workup

  1. temperatureat reflux of the solvent for 200 h
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-2af4e668ecac405f872f7132b3e85565
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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