Synthetic Route of 709652-82-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. A new synthetic method of this compound is introduced below.
In a vial was placed 2-amino-5-bromo-pyridine-3-carbonitrile (150 mg, 0.758 mmol), 4,4,5,5- tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (288 mg, 1.14 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (11.7 mg, 0.015 mmol), and potassium acetate (149 mg, 0.515 mmol. Degassed ACN (9.5 mL) was added, and the reaction mixture was vacuum purged and back-filled with N2 (3X). The vial was capped, and the reaction mixture was microwaved at 150C for 30 min and then cooled to room temperature. To the reaction mixture was then added (5R,8S)- 8-(2-chloropyrimidin-4-yl)-3-(2,6-difluorophenyl)-9,9-dimethyl-5,6,7,8-tetrahydro-5,8-methanocinnoline (201 mg, 0.504 mmol), sodium carbonate (137 mg, 1.29 mmol), potassium acetate (74.3 mg, 0.757 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (11.7 mg, 0.015 mmol), and water (3.8 mL). The vial was recapped, and the reaction mixture was microwaved at 120C for 30 min and then filtered through a pad of Celite to rid Pd solid. The Celite pad was rinsed well with iPrOAc, and the filtrate was diluted with iPrOAc. The biphasic solution was separated. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluted with methanol/isopropyl acetate followed by reverse phase prep-HPLC to give 120.4 mg of the title compound as a white solid. 1H NMR (DMSO- d6, 400 MHz): delta 9.21 (d, J = 2.3 Hz, 1H), 8.89 (d, J = 5.2 Hz, 1H), 8.69 (d, J = 2.3 Hz, 1H), 7.83 (s, 1H), 7.69- 7.57 (m, 2H), 7.47 (s, 2H), 7.35- 7.26 (m, 2H), 3.38- 3.23 (m, 2H), 2.49- 2.41 (m, 1H), 1.65- 1.56 (m, 1H), 1.33- 1.24 (m, 1H), 1.11 (s, 3H), 0.74 (s, 3H); LCMS ES+ 482.1 [M+1]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,709652-82-4, its application will become more common.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRONNER, Sarah M.; CRAWFORD, James J.; CRIDLAND, Andrew; CYR, Patrick; FAUBER, Benjamin; GANCIA, Emanuela; GOBBI, Alberto; HURLEY, Christopher; KILLEN, Jonathan; LEE, Wendy; RENE, Olivier; VAN NIEL, Monique Bodil; WARD, Stuart; WINSHIP, Paul; ZBIEG, Jason; (439 pag.)WO2018/83105; (2018); A1;,
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