With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.760207-83-8, name is 3-Bromo-5-chloropicolinonitrile, molecular formula is C6H2BrClN2, molecular weight is 217.45, as common compound, the synthetic route is as follows.Safety of 3-Bromo-5-chloropicolinonitrile
Synthesis of 5-chloro-3-vinylpicolinic acid A sealable vial was charged with 3-bromo-5-chloropicolinonitrile (700 mg, 3.22 mmol) and dichlorobis(triphenyl-phosphine)palladium(II) (271 mg, 0.386 mmol). The vial was evacuated and backfilled with nitrogen. 1,4-dioxane (5 mL) was added, followed by tri-n-butyl(vinyl)tin (1.225 mL, 3.86 mmol). The reaction mixture was heated to 100 C. The reaction mixture was diluted with water and EtOAc. The solvent was removed under reduced pressure. The residue was dissolved in EtOH (3 mL) and NaOH (1M, 6 mL). The cloudy solution was heated to 100 C. for 15 min. The reaction mixture was cooled to RT, the aqueous phase was separated and neutralized with 1 M HCl. The aqueous phase was back-extracted with EtOAc. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure to obtain 5-chloro-3-vinylpicolinic acid (120 mg, 0.654 mmol, 20.30% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 5.56 (d, J=11.11 Hz, 1H) 6.07 (d, J=17.54 Hz, 1H) 7.12 (dd, J=17.54, 11.11 Hz, 1H) 8.33 (d, J=2.19 Hz, 1H) 8.58 (d, J=2.19 Hz, 1H)
At the same time, in my other blogs, there are other synthetic methods of this type of compound,760207-83-8, 3-Bromo-5-chloropicolinonitrile, and friends who are interested can also refer to it.
Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
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