5-Bromo-2-iodo-3-methylpyridine Chemical Properties

Boiling point:

279.9±35.0 °C(Predicted)

Density 

2.171±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-0.22±0.20(Predicted)

Appearance

Colorless to light yellow Solid-Liquid Mixture

Safety Information

HS Code 

2933399990

5-Bromo-2-iodo-3-methylpyridine Usage And Synthesis

Uses

5-Bromo-2-iodo-3-methylpyridine can be used as NADPH oxidase inhibitors useful in treatment and prophylaxis of NOX-mediated diseases.

Synthesis

2,5-Dibromo-3-methylpyridine (M-12) (5.02 g, 20.0 mmol) was used as a raw material and dissolved in acetonitrile (50 mL). Subsequently, sodium iodide (12.0 g, 80.0 mmol) and acetyl chloride (2.85 mL, 40.0 mmol) were sequentially added to this solution. The reaction mixture was heated and stirred under reflux conditions for 24 hours. Upon completion of the reaction, it was cooled to room temperature, diluted with an appropriate amount of water and the pH was adjusted to 8 with saturated aqueous sodium bicarbonate solution to neutralize the reaction mixture. Extraction was carried out with ethyl acetate, the organic layer was collected and dried over anhydrous sodium sulfate, and the desiccant was removed by filtration. The solvent was removed by concentration under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent ratio: n-hexane/ethyl acetate=98:2→70:30) to afford the target product 5-bromo-2-iodo-3-methylpyridine (M-13) (5.76 g, 97% yield) as a red oil.

References

[1] Patent: EP3351533, 2018, A1. Location in patent: Paragraph 0321; 0322
[2] Patent: JP2018/145180, 2018, A. Location in patent: Paragraph 0315; 0316; 0317
[3] Patent: WO2014/39484, 2014, A1. Location in patent: Page/Page column 40; 41
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 9, p. 1117 - 1130
[5] Journal of the American Chemical Society, 2017, vol. 139, # 49, p. 18016 - 18023

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