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Ammonium formate → 4-Hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642215
Notes
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Reaction equation

HRID 642215 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[CH:14]=[C:13](Br)[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C([O-])=O.[NH4+]>[Pd].CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[CH:14]=[CH:13][N:12]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 684286672-Bromo-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 684267014-Hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterYield 82.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl Acetate
Solvent
2×

Procedure

A mixture of 2-bromo-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (34 mg, 0.094 mmol), 10% palladium on carbon (10 mg), ammonium formate (119 mg, 1.88 mmol) in EtOAc (2 ml) was refluxed overnight; then the mixture was diluted with EtOAc, the solids were filtered off, the filtrate was concentrated and the resulting residue was purified on column to give the title product (22 mg) as a clear oil; ESI MS (m/z): 283 (M+H+).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationthe solids were filtered off
  3. concentrationthe filtrate was concentrated
  4. customthe resulting residue was purified on column

Sources & evidence

ORD record
ord-60b07e474258486db2f599fcafd8d60f
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696223B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes