Imidazo[1,2-b]pyridazine, 6-bromo-

Uses

Imidazo[1,2-b]pyridazine, 6-bromo- is a heterocyclic derivative that can be used as a pharmaceutical intermediate.

Synthesis

GENERAL STEPS: To a solution of 6-bromopyridazin-3-amine (3.48 g, 20 mmol) in ethanol/water (5:1, 180 mL) was added 2-bromo-1,1-diethoxyethane (11.8 g, 60 mmol) followed by p-toluenesulfonic acid (20.6 mg, 0.12 mmol). The reaction mixture was stirred at 80 °C for 16 h. After completion of the reaction, the solvent was concentrated in vacuum by rotary evaporator. The resulting solid was washed with distilled water (4 mL), collected by filtration through a Büchner funnel and dried overnight in a vacuum oven at 40 °C to afford 6-bromoimidazo[1,2-b]pyridazine as a gray solid (3.9 g, 100% yield). Mass spectrum (ESI, positive ion mode) m/z: 198.1 [M + H]+; 1H NMR (400 MHz, CDCl3): δ 8.71 (d, J = 9.6 Hz, 1H), 8.44 (d, J = 1.6 Hz, 1H), 8.33 (d, J = 1.9 Hz, 1H), 7.97 (d, J = 9.6 Hz, 1H).

References

[1] Patent: US2014/134133, 2014, A1. Location in patent: Paragraph 0288