反応 #157940

反応方程式

2-chloro-3,5-dimethylpyrazine

sodium carbonate

1-naphthylboronic acid

→

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

収率 59.0%

溶媒

water

acetonitrile

water

反応条件

後処理

1. 1
   その他First, into a recovery flask equipped with a reflux pipe
2. 2
   その他This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 10 minutes
3. 3
   温度whereby heating
4. 4
   抽出an organic layer was extracted with dichloromethane
5. 5
   洗浄The obtained organic layer was washed with water
6. 6
   乾燥dried with magnesium sulfate
7. 7
   ろ過After the drying, the solution was filtered
8. 8
   workup.DISTILLATIONThe solvent of this solution was distilled off
9. 9
   その他the obtained residue was purified by silica gel column chromatography
10. 10
    その他to be produced
11. 11
    その他was obtained
12. 12
    その他Note that the irradiation with microwaves
13. 13
    その他a microwaves synthesis system (Discover, produced by CEM Corporation)
14. 14
    その他The synthesis scheme of Step 1

実験手順

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.

出典