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

HRID 642223Notes

Reaction equation

HRID 642223 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14](Br)=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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[CH:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 684284133-bromo-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 684278502-(4-Fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterYield 111.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (515 mg, 1.13 mmol), 10% Pd/C (116 mg), and ammonium formate (1.43 g, 22.62 mmol) in EtOAc was refluxed overnight; then filtered, the filtrate was washed with saturated sodium chloride aqueous solution, then the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated to give a pure titled product (476 mg); ESI MS (m/z): 377 (M+H+).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationthen filtered
  3. washthe filtrate was washed with saturated sodium chloride aqueous solution
  4. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-760362c9d51f4c25bfb83c11e3aa16d7
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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