3-Bromo-6-chloroimidazo[1,2-b]pyridazine Chemical Properties

Melting point:

156 °C

Density 

2.03

storage temp. 

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

form 

Solid

pka

0.73±0.30(Predicted)

Appearance

White to light yellow Solid

Safety Information

Safety Statements 

24/25

HS Code 

29339900

3-Bromo-6-chloroimidazo[1,2-b]pyridazine Usage And Synthesis

Uses

3-Bromo-6-chloroimidazo[1,2-b]pyridazine is a reagent in the synthesis of imidazopyridazine series of inhibitors of Plasmodium falciparum calcium-dependent protein kinase 1 (PfCDPK1).

Synthesis

General procedure for the synthesis of 3-bromo-6-chloroimidazo[1,2-b]pyridazine from 6-chloroimidazo[1,2-b]pyridazine: 478 mg (3.11 mmol) of 6-chloroimidazo[1,2-b]pyridazine was dissolved in 10 mL of chloroform under the protection of argon and cooled in an ice bath. Subsequently, 664 mg (3.73 mmol) of N-bromosuccinimide was slowly added. After addition, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was mixed with water and ethyl acetate, and the organic and aqueous phases were separated by the addition of saturated sodium bicarbonate solution. The aqueous phase was extracted three times with ethyl acetate. The organic phase was combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to afford the target product 3-bromo-6-chloroimidazo[1,2-b]pyridazine as an amorphous white solid, which could be used in subsequent reactions without further chromatographic purification.1H-NMR (CDCl3, molecular sieve dried): δ = 7.12 (d, 1H); 7.79 (s, 1H); 7.90 (d, 1H) ppm.

References

[1] Patent: US2009/93475, 2009, A1. Location in patent: Page/Page column 6
[2] Patent: WO2013/34570, 2013, A1. Location in patent: Page/Page column 74
[3] Patent: WO2013/41634, 2013, A1. Location in patent: Page/Page column 73; 78; 87
[4] Patent: WO2013/144189, 2013, A1. Location in patent: Page/Page column 56
[5] Patent: WO2013/149909, 2013, A1. Location in patent: Page/Page column 60-61

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