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

HRID 1785590Notes

Reaction equation

HRID 1785590 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[N:15][CH:16]=1)=[O:10])C1C=CC=CC=1.CO>[OH-].[Pd+2].[OH-].[Pd]>[NH:17]1[C:14]2=[N:15][CH:16]=[C:11]([C:9]([OH:10])=[O:8])[CH:12]=[C:13]2[CH:19]=[CH:18]1

Participants

5

Reactant 2

HCID 887MethanolHCID 57595581Benzyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

HCID 219070181H-Pyrrolo[2,3-b]pyridine-5-carboxylic acidYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalyst

Procedure

Into a round bottom flask was added compound 22 (55.0 mg, 0.000218 mol) and palladium hydroxide, 20 wt. % Pd on carbon, wet (20.0 mg, 0.000142 mol) and Methanol (5.0 mL, 0.12 mol) under an atmosphere of Hydrogen. The reaction mixture was stirred at room temperature overnight. Filtration and concentration gave product 15 (35 mg).

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-70c23076694c4c9490af5a7c39c65a97
Source dataset
uspto-grants-2009_03
Patent number
US07504509B2

Reaction notes

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