Reaktion #2260928

Reaktionsgleichung

2-chloro-3,5-dimethylpyrazine

sodium carbonate

7-phenylnaphthalene-2-boronic acid

→

3,5-Dimethyl-2-(7-phenylnaphthalen-2-yl)pyrazine

Ausbeute 65.0%

Lösungsmittel

Water

acetonitrile

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeFirst, into a recovery flask equipped with a reflux pipe
2. 2
   SonstigeThis reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 15 minutes
3. 3
   Temperaturso that heating
4. 4
   TemperaturThen, the reaction container was cooled to 50° C. or less
5. 5
   Extraktionthe organic layer was extracted with dichloromethane
6. 6
   WaschenThe obtained organic layer was washed with water
7. 7
   Trocknendried with magnesium sulfate
8. 8
   SonstigeThe solution which had been dried
9. 9
   Filtrationwas filtered
10. 10
    workup.DISTILLATIONThe solvent of this solution was distilled
11. 11
    Sonstigethe obtained residue was purified by silica gel column chromatography with a developing solvent of dichloromethane, whereby Hdm7p2npr, which
12. 12
    Sonstigeto be produced
13. 13
    Sonstigeto be obtained (as a white powder in 65% yield)
14. 14
    SonstigeNote that the microwave irradiation
15. 15
    Sonstigea microwave synthesis system (Discover, manufactured by CEM Corporation)
16. 16
    SonstigeThe synthesis scheme of Step 4

Vorschrift

First, into a recovery flask equipped with a reflux pipe were placed 0.62 g of 2-chloro-3,5-dimethylpyrazine, 1.07 g of 7-phenylnaphthalene-2-boronic acid, 0.46 g of sodium carbonate, 0.020 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 15 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 the obtained residue was purified by silica gel column chromatography with a developing solvent of dichloromethane, whereby Hdm7p2npr, which is the pyrazine derivative to be produced, was found to be obtained (as a white powder in 65% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 4 is illustrated in the following (d-5).

Quelle