Cesium carbonate → HCID 117732307, Verbindung

HRID 1772748

Reaktionsgleichung

Reaktionsgleichung von HRID 1772748
Br[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([Cl:9])=[N:4][CH:3]=1.Br[C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[N:15][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:8][C:6]1[N:7]=[C:2]([C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[N:15][CH:16]=2)[CH:3]=[N:4][C:5]=1[Cl:9]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 112447754-Boc-1-(5-bromo-2-pyridyl)piperazineHCID 569657236-Bromo-3-chloropyrazin-2-amine

Produkt 1

HCID 117732307HCID 117732307, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Into a 2 L 4-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of compound 90e (42.8 g, 206 mmol) in 1,4-dioxane (1 L), compound 90b (80.0 g, 206 mmol), Pd(dppf)Cl2 (7.53 g, 10.3 mmol) and Cs2CO3 (167 g, 514 mmol). The reaction mixture was stirred overnight at 90° C. Upon cooling, the reaction was quenched with water (100 mL). The resulting mixture was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The resultant residue was purified by flash column chromatography on silica gel (DCM/MeOH (100:3 v/v)) to obtain compound 90f as a yellow solid (23.0 g, 29% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C18H23ClN6O2: 391.2 (M+H). found 391.1.

Aufarbeitung

  1. customInto a 2 L 4-necked round-bottom flask, purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureUpon cooling
  4. customthe reaction was quenched with water (100 mL)
  5. extractionThe resulting mixture was extracted with DCM
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant residue was purified by flash column chromatography on silica gel (DCM/MeOH (100:3 v/v))

Quellen und Nachweise

ORD-Eintrag
ord-136fcc35055b407f892d7e9a44fa65c5
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249163B2

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