Cesium carbonate → 5-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one

HRID 2069734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069734
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.Br[C:13]1[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=[C:17]([Br:19])[CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:19][C:17]1[CH:18]=[C:13]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]([OH:11])([CH3:9])[CH3:10])=[CH:6][N:7]=2)[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 594737712-(6-Aminopyridin-3-yl)propan-2-ol

Produkt 1

HCID 594737935-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-oneAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a flame-dried seal tube reaction vial, dissolve 2-(6-Amino-pyridin-3-yl)-propan-2-ol (530 mg, 3.484 mmol) in anhydrous Dioxane (13 mL). Then add 3,5-Dibromo-1-methyl-1H-pyridin-2-one (1.022 g, 3.83 mmol), Cs2CO3 (3.4 g, 10.45 mmol) and Xantphos (0.2 g, 0.3482 mmol). Bubble argon through for 15 min before adding Pd(OAc)2 (39 mg, 0.1742 mmol). The tube as sealed and heated to 120° C. Reaction was kept at that temperature for 6 hrs. Reaction was then diluted with EtOAc (10 mL) and filtered through celite. Filter cake was washed with EtOAc (3×10 mL). The combined filtrate was concentrated and purified on ISCO column with 5-10% MeOH in 1/1 EtOAC/Hexane to afford 5-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one (710 mg, yield 60%) as green solid.

Aufarbeitung

  1. customIn a flame-dried seal tube
  2. customreaction vial
  3. customThe tube as sealed
  4. customReaction
  5. customReaction
  6. filtrationfiltered through celite
  7. filtrationFilter cake
  8. washwas washed with EtOAc (3×10 mL)
  9. concentrationThe combined filtrate was concentrated
  10. custompurified on ISCO column with 5-10% MeOH in 1/1 EtOAC/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-d6cc6ff042694801a73e352d2450de0e
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299077B2

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