8-Bromo-6-chloroimidazo[1,2-a]pyridine

Uses

8-Bromo-6-chloroimidazo[1,2-a]pyridine is used as an organic chemical synthesis intermediate.

Synthesis

3-Bromo-5-chloropyridin-2-amine (10 g, 49 mmol) and chloroacetaldehyde (50% aqueous, 12 mL, 98 mmol) were mixed in ethanol (100 mL) and the reaction was heated at 50 °C overnight. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated. To the concentrated residue was added acetone (30 mL) and stirred rapidly for 2 hours. The resulting solid was collected by filtration and dried to afford the target product 8-bromo-6-chloroimidazo[1,2-a]pyridine (10.0 g, 89% yield). Mass spectrometry analysis showed [M + H]+ peak of 231. 1H NMR (500 MHz, DMSO) data were as follows: δ 9.20 (s, 1H), 8.33 (s, 1H), 8.29 (s, 1H), 8.09 (s, 1H).

References

[1] Patent: US2013/116262, 2013, A1. Location in patent: Paragraph 0195; 0196; 0197
[2] Patent: WO2011/72064, 2011, A1. Location in patent: Page/Page column 74