Sodium Carbonate → HCID 58894567, Verbindung

HRID 1028355

Reaktionsgleichung

Reaktionsgleichung von HRID 1028355
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:18]2[CH:23]=[CH:22][C:21]([N:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C(#N)C>[CH3:8][C:7]1[C:2]([C:34]2[CH:33]=[CH:32][C:31]([N:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]3[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=3)=[CH:36][CH:35]=2)=[N:3][CH:4]=[C:5]([CH3:9])[N:6]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 11639307Diphenyl-(4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-phenyl)-amineHCID 116726802-Chloro-3,5-dimethylpyrazine

Produkt 1

HCID 58894567HCID 58894567, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Next, there were put 0.36 g of 2-chloro-3,5-dimethylpyrazine, 0.92 g of 4,4,5,5-tetramethyl-2-(4-diphenylaminophenyl)-1,3,2-dioxaborolane obtained in Step 1, 0.26 g of sodium carbonate, 0.011 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile in a recovery flask equipped with a reflux pipe. The air in the flask was replaced by argon. This reaction container was heated by microwave irradiation (2.45 GHz, 100 W) for 20 minutes. After that, the reaction container was cooled to 50° C. or lower, water was added to the reaction solution, and the organic layer was subjected to extraction with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled, and the obtained residue was purified by silica gel column chromatography using a mixed solvent of dichloromethane and ethyl acetate as a developing solvent, thereby obtaining the objective pyrazine derivative Hdmdpappr (white powder, 30% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, produced by CEM Corporation). The synthesis scheme of Step 2 is shown by (b-2).

Aufarbeitung

  1. customequipped with a reflux pipe
  2. temperatureThis reaction container was heated by microwave irradiation (2.45 GHz, 100 W) for 20 minutes
  3. extractionthe organic layer was subjected to extraction with dichloromethane
  4. washThe obtained organic layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter the drying, the solution was filtered
  7. distillationThe solvent of this solution was distilled
  8. customthe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3a6140d3fe854b9198a2aff6441ddd64
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735581B2

Verknüpfte Notizen

Wird geladen…