6-CHLORO-3-IODOIMIDAZO[1,2-B]PYRIDAZINE Chemical Properties

Density 

2.34

storage temp. 

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

form 

solid

pka

1.03±0.30(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C6H3ClIN3/c7-4-1-2-6-9-3-5(8)11(6)10-4/h1-3H

InChIKey

IWHCPHZAMFSDFM-UHFFFAOYSA-N

SMILES

C12=NC=C(I)N1N=C(Cl)C=C2

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

6-CHLORO-3-IODOIMIDAZO[1,2-B]PYRIDAZINE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 6-chloro-3-iodoimidazo[1,2-b]pyridazine using 6-chloroimidazo[1,2-b]pyridazine as starting material was as follows: 6-chloroimidazo[1,2-b]pyridazine (2.0 g, 13.0 mmol, 1.0 equiv) was dissolved in chloroform (20 mL) at room temperature. Subsequently, iodosuccinimide (2.9 g, 13.0 mmol, 1.0 eq.) was added to this solution and the reaction mixture was vigorously stirred overnight at room temperature. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate. The extract was purified by column chromatography, resulting in 3.3 g of yellow solid product in 90% yield. The structure of the product was confirmed by 1H NMR: δ 8.21 (d, J = 7.6 Hz, 1H), 7.96 (s, 1H), 7.41 (d, J = 7.6 Hz, 1H).

References

[1] Patent: US2014/256733, 2014, A1. Location in patent: Page/Page column 0227; 0230-0231
[2] MedChemComm, 2018, vol. 9, # 10, p. 1733 - 1745
[3] Patent: EP2818471, 2014, A1. Location in patent: Paragraph 0120; 0121
[4] Patent: WO2013/34048, 2013, A1. Location in patent: Page/Page column 77; 78
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2789 - 2798

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