Electric Literature of 716362-10-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 716362-10-6 as follows.
6-Chloro-4-methoxynicotinic acid (18) was prepared according to Ehara et al., ACS Med. Chem. Lett. 2014, 5, 787-792. To a suspension of this compound (3.87 g, 9.97 mmol) in oxalyl chloride (25 mL, 37 g, 291.5 mmol) was added DMF (0.8 mL) followed by anhydrous CH2C12(10 mL) and the reaction mixture was stirred 2 h at 60 C. Afterwards the reaction mixture was concentrated using the argon flow and the residue was dried under reduced pressure affording the respective chloroanhydride (4.0 g, 100% crude) which was immediately used for the next step.To a solution of this compound in hot EtOAc (100 mL) was added 2,3,5,6-tetrafluorophenol (2.92 g, 19.35 mmol; vigorous gas evolution was observed). Thereafter, the mixture was cooled to ambient temperature, Et3N (2.68 mL, 1.96 g, 19.35 mmol) was added dropwise and the resulting suspension was stirred for 1 h. Afterwards, the reaction mixture was washed with H20 (3 X20 mL), brine (2×20 mL), dried and concentrated under reduced pressure. The residue was taken up in CH2Cl2(70 mL), the suspension was filtered, the filter cake was washed with CH2Cl2(50 mL). The collected dichloromethane fraction was concentrated under reduced pressure. The residue was recrystallized from hexane affording 14 (2.6 g, 44%) as a colorless solid. The mother liquor was concentrated by reduced pressure and the residue was purified by column chromatography (CH2Cl2:hexane=8:2.5) giving the second crop of 14 (0.8 g, total 58%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,716362-10-6, its application will become more common.
Reference:
Patent; UNIVERSITAeT ZU KOeLN; NEUMAIER, Bernd; ZLATOPOLSKIY, Boris; KRAPF, Philipp; RICHARZ, Raphael; DRZEZGA, Alexander; (49 pag.)WO2019/175405; (2019); A1;,
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