Cesium carbonate → HCID 69663924, Verbindung

HRID 352356

Reaktionsgleichung

Reaktionsgleichung von HRID 352356
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:53]([N:56]1[C:64]2[C:59](=[CH:60][C:61]([O:66][CH3:67])=[C:62](Br)[CH:63]=2)[CH2:58][CH2:57]1)(=[O:55])[CH3:54].[CH3:68][N:69]1[C@H:74]([CH3:75])[CH2:73][NH:72][CH2:71][C@@H:70]1[CH3:76]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:53]([N:56]1[C:64]2[C:59](=[CH:60][C:61]([O:66][CH3:67])=[C:62]([N:72]3[CH2:73][C@H:74]([CH3:75])[N:69]([CH3:68])[C@H:70]([CH3:76])[CH2:71]3)[CH:63]=2)[CH2:58][CH2:57]1)(=[O:55])[CH3:54]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 219483751-Acetyl-6-bromo-5-methoxyindolineHCID 30720221(2R,6S)-1,2,6-Trimethylpiperazine

Produkt 1

HCID 69663924HCID 69663924, VerbindungAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

A mixture of palladium (II) acetate (500 mg), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.0 g) and cesium carbonate (10.3 g) in dry degassed 1,4-dioxane (120 ml) under argon was sonicated at 28° C. for 0.5 h producing a pink heterogeneous mixture. This was treated with D1 (6.0 g, 22 mmole) followed by cis-1,2,6-trimethylpiperazine (J. Med. Chem. 1968, 11, 592; 4.8 g, 38 mmole) and heated with rapid stirring at reflux for 70 h. The mixture was allowed to cool, filtered, then concentrated under vacuum. The residue was treated with water and extracted with EtOAc. The organic solution was then extracted with 1M HCl acid and the aqueous extract was basified by addition of K2CO3 and extracted with EtOAc. The extract was dried (Na2SO4) and concentrated under vacuum to leave an orange solid, which was chromatographed on silica gel eluting with 0-10% MeOH/DCM to afford the required product as a pale yellow solid (1.6 g, 23%).

Aufarbeitung

  1. customin dry
  2. customdegassed 1,4-dioxane (120 ml) under argon
  3. customwas sonicated at 28° C. for 0.5 h
  4. customproducing a pink heterogeneous mixture
  5. temperatureheated
  6. temperatureat reflux for 70 h
  7. temperatureto cool
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. additionThe residue was treated with water
  11. extractionextracted with EtOAc
  12. extractionThe organic solution was then extracted with 1M HCl acid
  13. extractionthe aqueous extract
  14. additionwas basified by addition of K2CO3
  15. extractionextracted with EtOAc
  16. dry with materialThe extract was dried (Na2SO4)
  17. concentrationconcentrated under vacuum
  18. customto leave an orange solid, which
  19. customwas chromatographed on silica gel eluting with 0-10% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-0e200c4f699442a2bd2ffad183f4181a
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747030B1

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