Sodium Carbonate → 3,5-Dimethyl-2-(4-naphthalen-2-yl-phenyl)pyrazine

HRID 2173741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173741
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O.C(#N)C>[CH3:8][C:7]1[C:2]([C:23]2[CH:22]=[CH:21][C:20]([C:11]3[CH:12]=[CH:13][C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:10]=3)=[CH:25][CH:24]=2)=[N:3][CH:4]=[C:5]([CH3:9])[N:6]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 116726802-Chloro-3,5-dimethylpyrazineHCID 453822584-(2-Naphthyl)phenylboronic Acid

Produkt 1

HCID 584610473,5-Dimethyl-2-(4-naphthalen-2-yl-phenyl)pyrazineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

First, into a recovery flask equipped with a reflux pipe were placed 0.55 g of 2-chloro-3,5-dimethylpyrazine, 0.96 g of 4-(2-naphthyl)phenylboronic acid, 0.41 g of sodium carbonate, 0.018 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 50 minutes, so that heating was performed. Then, the reaction container was cooled to 50° C. or less. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled, and recrystallized using methanol, whereby Hdm2nppr, which is the pyrazine derivative to be produced, was obtained (as a white powder in 85% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 3 is illustrated in the following (c-2).

Aufarbeitung

  1. customFirst, into a recovery flask equipped with a reflux pipe
  2. customThis reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 50 minutes
  3. temperatureso that heating
  4. temperatureThen, the reaction container was cooled to 50° C. or less
  5. extractionthe organic layer was extracted with dichloromethane
  6. washThe obtained organic layer was washed with water
  7. dry with materialdried with magnesium sulfate
  8. customThe solution which had been dried
  9. filtrationwas filtered
  10. distillationThe solvent of this solution was distilled
  11. customrecrystallized
  12. customto be produced
  13. customwas obtained (as a white powder in 85% yield)
  14. customNote that the microwave irradiation
  15. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  16. customThe synthesis scheme of Step 3

Quellen und Nachweise

ORD-Eintrag
ord-8047151310a541c9a48ee0f8b4127618
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056883B2

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