Ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate → 1H-Pyrrole-3-carboxylic acid, 5-(2-fluorophenyl)-, ethyl ester

HRID 1012381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012381
Cl[C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C.[C].[Pd]>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:4]1[NH:3][CH:2]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=1

Komponenten

4

Edukt 1

HCID 66924835Ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate

Produkt 1

HCID 669246981H-Pyrrole-3-carboxylic acid, 5-(2-fluorophenyl)-, ethyl esterAusbeute 18,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution (80 mL) of ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate (8.6 g) in ethanol was added 10% palladium carbon (50% containing water, 0.86 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 36 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (70 mL), 10% palladium carbon (50% containing water, 0.90 g) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=10:1→5:1) to give the title compound as a brown solid (yield 1.37 g, 18%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethanol (70 mL)
  4. addition10% palladium carbon (50% containing water, 0.90 g) was added
  5. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 60 hr
  6. filtrationThe reaction mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=10:1→5:1)

Quellen und Nachweise

ORD-Eintrag
ord-5d423231b96845de98cfd2f1ebcf8cba
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977488B2

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