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

HRID 562851Notes

Reaction equation

HRID 562851 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-a4d78e4337944a3c824efa5de88762ff
Source dataset
uspto-grants-2011_11
Patent number
US08067434B2

Reaction notes

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