Sodium Carbonate → (S)-4-(2-chlorophenyl)-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)oxazolidin-2-one

HRID 539113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539113
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[C@@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[Cl:22])[CH2:14][O:13][C:12]3=[O:23])=[N:7][C:6]=12.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[F:66][C:67]1[CH:72]=[C:71](B2OC(C)(C)C(C)(C)O2)[CH:70]=[CH:69][C:68]=1[C:82]1[N:86]=[CH:85][N:84]([CH2:87][O:88][CH2:89][CH2:90][Si:91]([CH3:94])([CH3:93])[CH3:92])[N:83]=1.C([O-])([O-])=O.[Na+].[Na+]>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.CCOC(C)=O.O1CCOCC1>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C@H:15]1[CH2:14][O:13][C:12](=[O:23])[N:11]1[C:8]1[CH:9]=[CH:10][N:5]2[N:4]=[CH:3][C:2]([C:71]3[CH:70]=[CH:69][C:68]([C:82]4[N:86]=[CH:85][N:84]([CH2:87][O:88][CH2:89][CH2:90][Si:91]([CH3:93])([CH3:92])[CH3:94])[N:83]=4)=[C:67]([F:66])[CH:72]=3)=[C:6]2[N:7]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67034012HCID 67034012, VerbindungHCID 67035102(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-chlorophenyl)oxazolidin-2-one

Produkt 1

HCID 67034362(S)-4-(2-chlorophenyl)-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)oxazolidin-2-oneAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-chlorophenyl) oxazolidin-2-one (50 mg, 0.13 mmol) were added Pd2 dba3 (5.8 mg, 0.0064 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (7.3 mg, 0.013 mmol), 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 (69 mg, 0.17 mmol), dioxane (1.2 mL) and 2M Na2CO3 (0.2 mL). The reaction was stirred for 2 hours at 80° C. in a sealed tube. After cooling, EtOAc and water were added. The organic phase was washed with brine and dried over MgSO4. The residue was purified by reverse phase chromatography (SP4, 12M, water/CH3CN 90:10 to 0:100, 20 column volumes) to yield (S)-4-(2-chlorophenyl)-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)oxazolidin-2-one (24 mg, 31% yield) as a pale yellow solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. customThe residue was purified by reverse phase chromatography (SP4, 12M, water/CH3CN 90:10 to 0:100, 20 column volumes)

Quellen und Nachweise

ORD-Eintrag
ord-b3101ec570e34a8b9186d39dca8f99db
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865726B2

Notizen zur Reaktion

Wird geladen…