7-CHLOROIMIDAZO[1,2-A]PYRIDINE Chemical Properties

Melting point:

49-51 ºC

Density 

1.35

storage temp. 

Inert atmosphere,Room Temperature

pka

5.21±0.50(Predicted)

Appearance

Light yellow to brown Solid

Safety Information

HS Code 

2933399990

7-CHLOROIMIDAZO[1,2-A]PYRIDINE Usage And Synthesis

Application

7-Chloro-imidazolium pyridine is an imidazopyridine or pyrimidine derivative. Imidazolidine or pyrimidine derivatives are nitrogen-containing heterocyclic compounds fused with a five-membered imidazolium ring and a six-membered pyridine or pyrimidine ring. They are important pharmaceutical intermediates with wide applications in the fields of medicine, pesticides, and chemicals.

Synthesis

Synthesis of 7-chloroimidazo[1,2-a]pyridine (Compound 65-3) [0000229]: To an ethanol (15 mL) suspension of Compound 65-2 (HCl) was added sodium bicarbonate powder (3.3 g, 38.4 mmol, 4 eq.) and 50% aqueous chloroacetaldehyde (2.26 g, 14.4 mmol, 1.5 eq.). The reaction mixture was heated to reflux for 4 hours followed by stirring at room temperature for 16 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. The residue was dissolved in water (10 mL) and ethyl acetate (10 mL) for liquid-liquid separation. The aqueous phase was further extracted with ethyl acetate (2 x 5 mL). All organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give compound 65-3 as a dark yellow oil (980 mg, 89% yield).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 750 - 756
[2] Patent: WO2013/123215, 2013, A2. Location in patent: Paragraph 0000229
[3] Patent: EP2565185, 2013, A1. Location in patent: Paragraph 0114-0115
[4] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 123 - 131
[5] Patent: WO2008/78100, 2008, A2. Location in patent: Page/Page column 93-94

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