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

HRID 642223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642223
[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]

Komponenten

5

Edukt 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

Produkt 1

HCID 684278502-(4-Fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterAusbeute 111,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-760362c9d51f4c25bfb83c11e3aa16d7
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

Notizen zur Reaktion

Wird geladen…