Synthesis
3-Fluoropyridine (25 g, 257 mmol) was slowly added dropwise to a solution of tetrahydrofuran (600 mL) containing butyl lithium (270 mmol) and diisopropylamine (27.4 g, 271 mmol) at -78 °C. The reaction mixture was stirred continuously at this temperature for 1 hour. Subsequently, crushed dry ice was added to the reaction system and gradually warmed to room temperature over 1 hour. Upon completion of the reaction, the pH of the reaction solution was adjusted to 5 with an aqueous solution of hydrogen chloride and acidified. The resulting precipitate was collected by filtration and dried. The final 3-fluoroisonicotinic acid (25.2 g, 179 mmol, 70% yield) was obtained as colorless crystals.
References
[1] Patent: WO2006/36015, 2006, A2. Location in patent: Page/Page column 121-122
[2]Cheng, Z., Dong, L., Li, Y., Yan, H., Zhang, J., Xiang, S., & Zhang, Z. (2025). Lewis Acidity‐Enhanced Metal‐Organic Frameworks as High‐Efficiency Cathode Catalysts for Advanced Li‐CO<sub>2</sub> Batteries. Advanced Functional Materials, 35(35).
https://doi.org/10.1002/adfm.202504330 [3]Sutovska, M., Kocmalova, M., Joskova, M., Adamkov, M., & Franova, S. (2015). The effect of long-term administered CRAC channels blocker on the functions of respiratory epithelium in guinea pig allergic asthma model. General physiology and biophysics, 34(02), 167–176.
https://doi.org/10.4149/gpb_2014031 [4]Šutovská, M., Kocmálová, M., Adamkov, M., Výbohová, D., Mikolka, P., Mokrá, D., Hatok, J., & Fraňová, M. A. S. (2013). The long-term administration of Orai 1 antagonist possesses antitussive, bronchodilatory and anti-inflammatory effects in experimental asthma model. General physiology and biophysics, 32(02), 251–259.
https://doi.org/10.4149/gpb_2013018
