Triethylamine → methyl 4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate

HRID 1012455

Reaktionsgleichung

Reaktionsgleichung von HRID 1012455
Cl[C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:5]([F:11])[C:6]=1[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C>CO.[C].[Pd]>[F:11][C:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:2][NH:3][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 2

HCID 8471TriethylamineHCID 66974454methyl 2-chloro-4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate

Produkt 1

HCID 66974524methyl 4-fluoro-5-phenyl-1H-pyrrole-3-carboxylateAusbeute 86.784,898 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Methyl 2-chloro-4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate (0.92 mg), 10% palladium carbon (50% containing water, 0.20 g) and triethylamine (0.56 mL) were suspended in methanol (30 mL), and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 hr. The reaction mixture was filtered through celite, and the insoluble material was washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=19:1→1:1) to give the title compound as a colorless solid (yield 0.69 g, 87%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe insoluble material was washed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=19:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4533ef72fef24f07a856e7e415b9f822
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977488B2

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