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

HRID 539055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539055
Cl[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)[CH2:14][O:13][C:12]3=[O:22])=[N:7][C:6]=12.C(=O)([O-])[O-].[Na+].[Na+].[F:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][C:31]=1[C:45]1[N:49]=[CH:48][N:47]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[N:46]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>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].O>[F:29][C:30]1[CH:35]=[C:34]([C:2]2[CH:3]=[N:4][N:5]3[CH:10]=[CH:9][C:8]([N:11]4[CH:15]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=5)[CH2:14][O:13][C:12]4=[O:22])=[N:7][C:6]=23)[CH:33]=[CH:32][C:31]=1[C:45]1[N:49]=[CH:48][N:47]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[N:46]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67034012HCID 67034012, VerbindungHCID 670346473-(3-Chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one

Produkt 1

HCID 670347823-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-oneAusbeute 48,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-(3-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (0.42 g, 1.3 mmol) in dioxanes was added sodium carbonate solution (2.0 M, 3.3 ml, 6.7 mmol) and 3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (0.61 g, 1.5 mmol) and the reaction bubbled with nitrogen for 30 minutes, followed by the addition of XPHOS (0.63 g, 1.3 mmol) and Pd2 dba3 (1.2 g, 1.3 mmol), and the reaction stirred at 80° C. for 3 hours. The reaction was poured into water and extracted into EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by normal phase chromatography using a gradient eluent from 25% EtOAc in hexane to EtOAc to yield 3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (0.36 g, 0.63 mmol, 47% yield).

Aufarbeitung

  1. customthe reaction bubbled with nitrogen for 30 minutes
  2. extractionextracted into EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by normal phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-26f21f4f38be4c47adc23c0261405edc
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865726B2

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