Reaktion #157940

Reaktionsgleichung

2-chloro-3,5-dimethylpyrazine

sodium carbonate

1-naphthylboronic acid

→

2-(1-naphthyl)-3,5-dimethylpyrazine

Ausbeute 59.0%

Lösungsmittel

water

acetonitrile

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeFirst, into a recovery flask equipped with a reflux pipe
2. 2
   SonstigeThis reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 10 minutes
3. 3
   Temperaturwhereby heating
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
   FiltrationAfter the drying, the solution was filtered
8. 8
   workup.DISTILLATIONThe solvent of this solution was distilled off
9. 9
   Sonstigethe obtained residue was purified by silica gel column chromatography
10. 10
    Sonstigeto be produced
11. 11
    Sonstigewas obtained
12. 12
    SonstigeNote that the irradiation with microwaves
13. 13
    Sonstigea microwaves synthesis system (Discover, produced by CEM Corporation)
14. 14
    SonstigeThe synthesis scheme of Step 1

Vorschrift

First, into a recovery flask equipped with a reflux pipe were put 2.05 g of 2-chloro-3,5-dimethylpyrazine, 2.48 g of 1-naphthylboronic acid, 1.53 g of sodium carbonate, 0.066 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 10 minutes, whereby heating was performed. After that, 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 the drying, the solution was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using dichloromethane as a developing solvent. Accordingly, Hdm1npr (a light orange powder, 59% yield), which was the substance to be produced, was obtained. Note that the irradiation with microwaves was performed using a microwaves synthesis system (Discover, produced by CEM Corporation). The synthesis scheme of Step 1 is shown in (a-1) below.

Quelle