3-(Acetylamino)-5-bromopyridine

Synthesis

To a solution of 3-amino-5-bromopyridine (1.0 g, 5.78 mmol) and pyridine (1.3 mL, 12.9 mmol) in dichloromethane (DCM, 5 mL) was added acetic anhydride (0.6 mL, 6.358 mmol) dropwise. The reaction mixture was stirred at room temperature for 17 hours. Upon completion of the reaction, the mixture was concentrated and the crude product was purified by normal-phase column chromatography with an elution gradient of 0-75% ethyl acetate (EtOAc)/heptane to afford N-(5-bromopyridin-3-yl)acetamide (1.18 g, 95% yield).

References

[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 1, p. 83 - 89
[2] Patent: US2014/323468, 2014, A1. Location in patent: Paragraph 0601
[3] Patent: CN103601745, 2017, B. Location in patent: Paragraph 0035; 0036
[4] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1062,1068
[5] Journal fuer Praktische Chemie (Leipzig), 1933, vol. <2> 138, p. 244,257