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

HRID 642237Notes

Reaction equation

HRID 642237 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:13](Br)[N:12]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C([O-])=O.[NH4+]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:13][N:12]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 684282762-bromo-1-(4-fluoro-phenyl)-4-hydroxy-3-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 684282261-(4-Fluoro-phenyl)-4-hydroxy-3-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-bromo-1-(4-fluoro-phenyl)-4-hydroxy-3-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (514 mg, 1.13 mmol), 10% Pd—C (80 mg), and ammonium formate (1.42 g, 22.6 mmol) in EtOAc (15 mL) was refluxed for two days; then the catalysts were filtered off, the filtrate was concentrated, the left residue was purified on column to give the desired title product, ESI MS (m/z): 377 (M+H+).

Workup

  1. temperaturewas refluxed for two days
  2. filtrationthen the catalysts were filtered off
  3. concentrationthe filtrate was concentrated
  4. customthe left residue was purified on column

Sources & evidence

ORD record
ord-a3f505ea38bc425b928cfdf911ecd6ec
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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