Reaktion #619074

Reaktionsgleichung

2-chloro-3,5-dimethylpyrazine

sodium carbonate

2-naphthylboronic acid

→

2-(2-naphthyl)-3,5-dimethylpyrazine

Ausbeute 56.0%

Lösungsmittel

water

acetonitrile

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeFirst, to a recovery flask equipped with a reflux pipe
2. 2
   SonstigeThis reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 10 minutes
3. 3
   Temperaturto be heated
4. 4
   Extraktionan organic layer was extracted with dichloromethane
5. 5
   WaschenThe obtained organic layer was washed with water
6. 6
   Trocknendried with magnesium sulfate
7. 7
   SonstigeAfter drying
8. 8
   Filtrationthe solution was filtrated
9. 9
   workup.DISTILLATIONThe solvent of this solution was distilled off
10. 10
    Sonstigethe residue obtained by distillation
11. 11
    Sonstigewas purified by silica gel column chromatography
12. 12
    Sonstigewas obtained
13. 13
    SonstigeFor the irradiation with a microwave
14. 14
    Sonstigea microwave synthesis system (Discover, manufactured by CEM Corporation)
15. 15
    SonstigeA synthesis scheme of Step 1

Vorschrift

First, to a recovery flask equipped with a reflux pipe were placed 2.25 g of 2-chloro-3,5-dimethylpyrazine, 2.71 g of 2-naphthylboronic acid, 1.67 g of sodium carbonate, 0.072 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile, and the atmosphere in the flask was replaced with argon. This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 10 minutes to be heated. Then, water was added to this solution, and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After drying, the solution was filtrated. The solvent of this solution was distilled off and the residue obtained by distillation was purified by silica gel column chromatography using dichloromethane as a developing solvent. In this way, Hdm2npr (a light orange powder, yield: 56%), which was a target substance, was obtained. For the irradiation with a microwave, a microwave synthesis system (Discover, manufactured by CEM Corporation) was used. A synthesis scheme of Step 1 is shown in the following (B-1).

Quelle