Water → trans-Ethyl 2-(5-fluoro-2-methyl-2h-indazol-4-yl)cyclopropanecarboxylate

HRID 1639782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639782
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH3:19])[N:15]=2)[C:11]=1/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23].O>CS(C)=O>[F:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH3:19])[N:15]=2)[C:11]=1[C@@H:20]1[CH2:4][C@H:21]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 66720771ethyl (2E)-3-(5-fluoro-2-methyl-2H-indazol-4-yl)acrylate

Produkt 1

HCID 131729435trans-Ethyl 2-(5-fluoro-2-methyl-2h-indazol-4-yl)cyclopropanecarboxylateAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel3×

Versuchsvorschrift

To a suspension of sodium hydride (0.793 g, 18.2 mmol) in dimethyl sulfoxide (100 mL) was added a solution of trimethylsulfoxonium iodide (4.00 g, 18.2 mmol) in dimethyl sulfoxide (100 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added a solution of ethyl (2E)-3-(5-fluoro-2-methyl-2H-indazol-4-yl)acrylate (4.10 g, 16.5 mmol) in dimethyl sulfoxide (130 mL) at 0° C., and the mixture was stirred at room temperature for 14 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/3) to give the title compound (2.00 g, yield 46%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 14 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/3)

Quellen und Nachweise

ORD-Eintrag
ord-01782f96316946ada08ba4c177148789
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110585B2

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