3-BROMOIMIDAZO[1,2-B]PYRIDAZINE Chemical Properties

Melting point:

148.0 to 152.0 °C

Density 

1.89

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.35±0.30(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C6H4BrN3/c7-5-4-8-6-2-1-3-9-10(5)6/h1-4H

InChIKey

KJQVHOFAWISYDO-UHFFFAOYSA-N

SMILES

C12=NC=C(Br)N1N=CC=C2

CAS DataBase Reference

18087-73-5

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

HS Code 

29339900

3-BROMOIMIDAZO[1,2-B]PYRIDAZINE Usage And Synthesis

Uses

3-Bromoimidazo[1,2-B]pyridazine is a pharmaceutical intermediate compound. It is used in the preparation of Ponatinib, a tyrosine kinase inhibitor (TKI), which is used in the treatment of chronic myeloid leukaemia (CML) and Philadelphia chromosome-positive acute lymphoblastic leukaemia (Ph+ ALL).

Synthesis

Imidazo[1,2-b]pyridazine (6.0 g, 50.4 mmol) was used as starting material, and N-bromosuccinimide (NBS, 6.0 g, 75.6 mmol) and a catalytic amount of azobisisobutyronitrile (AIBN) were added in 50 mL of chloroform. The reaction mixture was heated and refluxed for 2 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature and subsequently stirred under ice bath conditions to promote precipitation. The precipitate was separated by filtration and the filtrate was concentrated to afford the target product 3-bromoimidazo[1,2-b]pyridazine as a pale yellow solid in 75% yield.

References

[1] Patent: CN105418615, 2016, A. Location in patent: Paragraph 0079 ; 0080 ; 0081; 0082; 0083; 0084
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 23, p. 5830 - 5835
[3] Patent: EP2818471, 2014, A1. Location in patent: Paragraph 0122; 0123
[4] Synthesis, 1981, # 12, p. 987 - 989
[5] Patent: WO2016/210036, 2016, A1. Location in patent: Page/Page column 107

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