Reference of 80517-21-1,Some common heterocyclic compound, 80517-21-1, name is 4-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 106(1)2-Amino-4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamide (106a)Compound (6b) (0.335 g) was dissolved in DMF (8.6 mL), and sodium hydride (0.097 g, a 55% dispersion in paraffin liquid) was added to the resulting solution at 0 C., followed by stirring for 30 min. Then, 4-fluoro-2-nitrobenzonitrile was added to the reaction solution, followed by stirring at 60 C. for 30 min. Water was added to the reaction solution, and the precipitate was collected by filtration and washed by sprinkling water to obtain 4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile (0.5 g, 85%). 4-{4-Chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile (0.35 g) and ammonium chloride (0.35 g) were dissolved in a solvent mixture of THF (3 mL), methanol (3 mL), and water (3 mL). Iron (0.57 g) was added to the resulting solution, followed by stirring at 70 C. for 1 hr. Insoluble matters were filtered by celite, and the solvent was distilled away. The precipitate was washed with water and was collected by filtration to obtain compound (106a) (0.32 g, 95%) as a white solid.1H-NMR (DMSO-d6) delta: 8.57 (1H, d, J=4.88 Hz), 7.70 (1H, d, J=9.27 Hz), 7.60 (1H, d, J=1.95 Hz), 7.47 (1H, d, J=4.88 Hz), 7.45 (1H, dd, J=9.27, 1.95 Hz), 6.92 (2H, brs), 3.73 (1H, tt, J=6.83, 6.83 Hz), 1.43 (6H, d, J=6.83 Hz); LRMS (ESI) m/z 330 [M+H]+.
The synthetic route of 80517-21-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; US2012/108589; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts