Methyl 3-broMo-6-chloropyrazine-2-carboxylate Chemical Properties

Melting point:

35-36 °C

Boiling point:

292.4±35.0 °C(Predicted)

Density 

1.772±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-3.78±0.10(Predicted)

Appearance

White to light yellow <35°C Solid,>36°C Liquid

Methyl 3-broMo-6-chloropyrazine-2-carboxylate Usage And Synthesis

Uses

Methyl 3-broMo-6-chloropyrazine-2-carboxylate is an important intermediate for the synthesis of a class of antitumour drugs, SHP2 inhibitors, which can be used in the pharmaceutical development process.

Synthesis

The general procedure for the synthesis of methyl 3-bromo-6-chloropyrazine-2-carboxylate from methyl 3-amino-6-chloropyrazine-2-carboxylate was as follows: 100 mL of acetic acid was added to a 500 mL three-necked flask and cooled to 0 °C. Methyl 3-amino-6-chloropyrazine-2-carboxylate (20 g, 0.11 mol) was slowly added dropwise to 100 mL of aqueous hydrogen bromide solution at 0 °C. The dropwise addition process was continued for 30 min to ensure complete reaction. Subsequently, 50 mL of aqueous sodium nitrite (20.7 g, 0.33 mol) was slowly added dropwise while maintaining 0°C. After 30 minutes of reaction, the completion of the reaction was confirmed and 30 mL of 10% sodium bisulfite solution was added to terminate the reaction. The reaction mixture was extracted with ethyl acetate (200 mL x 2 times), the organic phases were combined and dried with 20 g of anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give methyl 3-bromo-6-chloropyrazine-2-carboxylate (23.3 g, 87% yield) as a white solid.

References

[1] Patent: CN108101857, 2018, A. Location in patent: Paragraph 0035-0037

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