Cesium carbonate → HCID 68870828, Verbindung

HRID 730003

Reaktionsgleichung

Reaktionsgleichung von HRID 730003
[C:1]([C:5]1[O:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:18]1[N:23]=[C:22]2[N:24]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:25]([NH2:27])=[N:26][C:21]2=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([C:5]1[O:6][C:7]([C:18]2[N:23]=[C:22]3[N:24]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:25]([NH2:27])=[N:26][C:21]3=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 668690432-tert-Butyl-4-(4-fluorophenyl)oxazoleHCID 86063644HCID 86063644, Verbindung

Produkt 1

HCID 68870828HCID 68870828, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Bubble with nitrogen a suspension of 2-tert-butyl-4-(4-fluorophenyl)oxazole (0.145 g, 0.66 mmol), 5-bromo-3-isobutyl-3H-imidazo[4,5-b]pyridin-2-ylamine (0.355 g, 1.32 mmol), cesium carbonate (6.06 g, 18.6 mmol), palladium (II) acetate (0.201 g, 10%) and triphenylphosphine (0.14 g, 0.07 mmol) in DMF (1.5 mL). Heat the reaction at 100° C. overnight, cool to RT and partition between EtOAc and saturated aqueous NaCl. Wash the organic layer with saturated aqueous NaCl. Dry with Na2SO4, filter, concentrate, and purify (silica gel chromatography, eluting with 2% of 2M ammonia/MeOH in CH2Cl2 to give the title compound (0.07 g, 34%).

Aufarbeitung

  1. customBubble with nitrogen
  2. temperatureHeat
  3. customthe reaction at 100° C. overnight
  4. custompartition between EtOAc and saturated aqueous NaCl
  5. washWash the organic layer with saturated aqueous NaCl
  6. dry with materialDry with Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify (silica gel chromatography
  10. washeluting with 2% of 2M ammonia/MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-ebea77b7d7c54cd391eaca0d172e8e47
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582652B2

Verknüpfte Notizen

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