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Dimethylacetamide → methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate

HRID 1947373
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1947373
Br[C:2]1[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([S:12][CH2:13][CH3:14])=[CH:8][C:7]2=[O:15].[F:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([F:28])[CH:27]=1)[NH2:24].[CH3:29][C:30](N(C)C)=O>O.C(OCC)(=O)C>[F:20][C:21]1[CH:22]=[C:23]([NH:24][CH:29]([C:2]2[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=[C:6]3[C:11]=2[O:10][C:9]([S:12][CH2:13][CH3:14])=[CH:8][C:7]3=[O:15])[CH3:30])[CH:25]=[C:26]([F:28])[CH:27]=1
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Komponenten

5

Edukt 3

HCID 31374DimethylacetamideHCID 965953,5-DifluoroanilineHCID 58235026methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate

Produkt 1

HCID 58235050methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22728543
Water ethylacetate
Lösungsmittel

Versuchsvorschrift

Methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate (850 mg, 2.29 mmol, prepared as described in Example 9) and 3,5-difluoroaniline (621 mg, 4.81 mmol) in DMA (10 mL) were stirred at 50° C. overnight. The reaction mixture was diluted with water/ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 25% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate (550 mg, 57%) as a off-white solid. Mass Spectrum: M+H+ 420.

Aufarbeitung

  1. washThe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography on silica gel eluting with 0 to 25% ethyl acetate in dichloromethane
  5. customThe solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-36e309fc3ea243d88dfc0df43df9e0c4
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399460B2

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