Uses
2,6-Dibromopyridine-4-carboxylic Acid is an analog of 2,6-Dichloroisonicotinic acid which binds and inhibits tobacco catalase activity.
Synthesis
General procedure for the synthesis of 2,6-dibromopyridine-4-carboxylic acid from citrazinic acid: Citrazinic acid (2.33 g, 0.015 mol) was mixed with phosphorus tribromide and heated to 180 °C under nitrogen protection for 3 hours. After completion of the reaction, the reaction mixture was cooled and quenched carefully with ice water. The reaction mixture was filtered and the aqueous phase was extracted with dichloromethane (4 x 40 ml). The solid fraction was continuously extracted in a Soxhlet extractor using dichloromethane for 12 hours. The directly extracted organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give 2.2 g of slightly red solid. The organic phase of Soxhlet extraction was similarly dried with anhydrous sodium sulfate, filtered and concentrated to give 0.5 g of a slightly red solid. The two fractions of 2,6-dibromoisonicotinic acid (64% total yield) were combined after confirmation of structural identity by NMR hydrogen spectroscopy (CDCl3, δ 8.04, 2H, s).
References
[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5079 - 5093
[2] Tetrahedron, 2007, vol. 63, # 2, p. 291 - 298
[3] Organic and Biomolecular Chemistry, 2005, vol. 3, # 8, p. 1460 - 1467
[4] Patent: WO2005/84439, 2005, A1. Location in patent: Page/Page column 35
[5] Synthesis, 2000, # 8, p. 1138 - 1142
