Sodium Carbonate → (S)-4-ethyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one

HRID 539065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539065
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[C@@H:15]([CH2:16][CH3:17])[CH2:14][O:13][C:12]3=[O:18])=[N:7][C:6]=12.CC1(C)C(C)(C)OB([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[N:37]=[CH:36][N:35]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[N:34]=3)=[CH:29][CH:28]=2)O1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:16]([C@H:15]1[CH2:14][O:13][C:12](=[O:18])[N:11]1[C:8]1[CH:9]=[CH:10][N:5]2[N:4]=[CH:3][C:2]([C:27]3[CH:28]=[CH:29][C:30]([C:33]4[N:37]=[CH:36][N:35]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[N:34]=4)=[CH:31][CH:32]=3)=[C:6]2[N:7]=1)[CH3:17]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 595255703-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazoleHCID 67033956(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one

Produkt 1

HCID 68088869(S)-4-ethyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-oneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a sealed tube was added (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one (0.100 g, 0.321 mmol), 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (0.168 g, 0.418 mmol) and 2.0 M Na2CO3 (0.482 mL, 0.964 mmol) in dioxane (1.6 mL). The mixture was degassed by bubbling N2 through the solution. Pd2 dba3 (0.0147 g, 0.0161 mmol), and dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.0153 g, 0.0321 mmol) were added and the vessel was sealed under a N2 atmosphere. The mixture was heated at 90° C. for 18 hours. The reaction mixture was cooled to ambient temperature, filtered through glass fiber filter paper, concentrated and purified on silica gel (1-55% EtOAc in DCM) to provide (S)-4-ethyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.076 g, 47% yield) as a yellow gum.

Aufarbeitung

  1. customThe mixture was degassed
  2. customby bubbling N2 through the solution
  3. customthe vessel was sealed under a N2 atmosphere
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. filtrationfiltered through glass fiber
  6. filtrationfilter paper
  7. concentrationconcentrated
  8. custompurified on silica gel (1-55% EtOAc in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-1e3ef9dc77dc439c913624604e1cf6de
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865726B2

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