Cesium carbonate → HCID 90412745, Verbindung

HRID 1522048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522048
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][C:16]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)=[CH:17][C:10]=23)O1.Br[C:33]1[N:38]=[C:37]([NH2:39])[CH:36]=[N:35][CH:34]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[NH2:39][C:37]1[N:38]=[C:33]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][C:16]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)=[CH:17][C:10]=23)[CH:34]=[N:35][CH:36]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 126931822-Amino-6-bromopyrazineHCID 90413258HCID 90413258, Verbindung

Produkt 1

HCID 90412745HCID 90412745, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of Example 21A (500 mg, 1.2 mmol), 6-bromopyrazin-2-amine (244 mg, 1.4 mmol), bis(triphenylphosphine)palladium(ii) chloride (82 mg, 0.1 mmol), tricyclohexylphosphine (33 mg, 0.1 mmol) and cesium carbonate (1.2 g, 3.5 mmol) was purged with nitrogen, then anhydrous dioxane (60 ml) was added. The mixture was heated at 100° C. overnight. The reaction was cooled to room temperature and filtrated, and the solid was washed with dichloromethane (200 mL). The filtrate was concentrated and purified by flash chromatography on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate (30%) to provide the title compound. MS (ESI+) m/z 395 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltrated
  3. washthe solid was washed with dichloromethane (200 mL)
  4. concentrationThe filtrate was concentrated
  5. custompurified by flash chromatography on silica gel using an ISCO Companion
  6. washeluting with heptanes/ethyl acetate (30%)

Quellen und Nachweise

ORD-Eintrag
ord-c816803ab5c44db384979131113b5bcd
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073922B2

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