Potassium Carbonate → HCID 66810464, Verbindung

HRID 1097533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097533
F[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[NH:23][C:24](=[O:36])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:2]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:18][C:17]=1[NH:23][C:24](=[O:36])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 11217860Methyl 2-Fluoro-5-nitrobenzoateHCID 66810436N-(2-Fluoro-5-hydroxyphenyl)-3-(trifluoromethyl)benzeneacetamide

Produkt 1

HCID 66810464HCID 66810464, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-fluoro-5-nitrobenzoate (1.65 g, 8.29 mmol) and N-(2-fluoro-5-hydroxyphenyl)-2-[3-(trifluoromethyl)phenyl]acetamide (2.60 g, 8.30 mmol) produced in Example 53(i) in N,N-dimethylformamide (17 mL) was added potassium carbonate (1.72 g, 12.5 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate (90 mL), washed successively with water (2×90 mL) and saturated brine (90 ml), and dried over anhydrous magnesium sulfate. Insoluble material was filtered off. The obtained organic layer was purified by basic silica gel column chromatography (eluate: ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (3.78 g, 93%) as a brown oil.

Aufarbeitung

  1. washwashed successively with water (2×90 mL) and saturated brine (90 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationInsoluble material was filtered off
  4. customThe obtained organic layer was purified by basic silica gel column chromatography (eluate: ethyl acetate)
  5. concentrationthe obtained solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e77f2103b9f6428daaaddee972bec6b2
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143258B2

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