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Hexane → {[6-Chloro-2-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]methyl}-4-(2,2-difluoro-vinyl)-pyrrolidin-2-one

HRID 1926777
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1926777
[H-].[Na+].CCCCCC.[F:9][C:10]([F:18])=[CH:11][CH:12]1[CH2:16][NH:15][C:14](=[O:17])[CH2:13]1.Br[CH2:20][C:21]1[N:25]2[N:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:24]2=[N:23][C:22]=1[C:31]([F:34])([F:33])[F:32]>C1COCC1.O>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]2[N:25]([C:21]([CH2:20][N:15]3[CH2:16][CH:12]([CH:11]=[C:10]([F:18])[F:9])[CH2:13][C:14]3=[O:17])=[C:22]([C:31]([F:34])([F:33])[F:32])[N:23]=2)[N:26]=1
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Komponenten

7

Edukt 4

HCID 8058HexaneHCID 24758Sodium hydride3×HCID 17948959HCID 17948959, VerbindungHCID 536291543-(Bromomethyl)-6-chloro-2-(trifluoromethyl)imidazo[1,2-b]pyridazine

Produkt 1

HCID 15952753{[6-Chloro-2-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]methyl}-4-(2,2-difluoro-vinyl)-pyrrolidin-2-oneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Sodium hydride (60% wt mineral oil dispersion, 0.82 g, 1.3 eq, 20.5 mmol) is washed three times by hexane (15 ml). THF (15 ml) is added at room temperature to this clean sodium hydride, a solution of 4-(2,2-difluorovinyl)pyrrolidin-2-one x98 (3.42 g, 23 mmol, 1.4 eq) and 3-(bromomethyl)-6-chloro-2-(trifluoromethyl)imidazo[1,2-b]pyridazine x36 (4.97 mg, 15.8 mmol, 1 eq) in THF (15 ml). After 3 hours of stirring at room temperature, a small amount of sodium hydride is added in order to complete the reaction and stirring is pursue overnight. Water (25 ml) is then added to the mixture and THF is removed evaporation under reduced pressure. The aqueous layer is extracted by ethyl acetate (2×50 ml), the resulting organic layer is dried over MgSO4, filtered and concentrated to dryness. The residue is purified by preparative chromatography (benzine/AcOEt:50/50) to afford 4.33 g of {[6-chloro-2-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]methyl}-4-(2,2-difluoro-vinyl)-pyrrolidin-2-one 33.

Aufarbeitung

  1. customthe reaction
  2. stirringstirring
  3. waitis pursue overnight
  4. customis removed
  5. customevaporation under reduced pressure
  6. extractionThe aqueous layer is extracted by ethyl acetate (2×50 ml)
  7. dry with materialthe resulting organic layer is dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe residue is purified by preparative chromatography (benzine/AcOEt:50/50)

Quellen und Nachweise

ORD-Eintrag
ord-cc981fe5fe84479e86505c003256258d
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08183241B2

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