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. 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate. A new synthetic method of this compound is introduced below., Safety of Methyl 5-bromo-2-chloronicotinate
A suspension of zinc (5.0g) in 4N HCl (10mL) was stirred at 30C for 10min and then filtered. The residue was crushed to yield fine particles and then washed with water (5¡Á) and acetone (2¡Á). The activated zinc was then dried in vacuo for 24h. (0020) A solution of 3-chloro-2-flurobenzyl bromide (1.12g, 5mmol) in THF (3mL) was added dropwise to suspension of activated zinc (0.98g, 15mmol), 1,2-dibromoethane (0.034mL, 0.4mmol), trimethylchlorosilane (0.038mL, 0.3mmol) and THF (1.5mL) at 23C. The reaction was heated to 45C and maintained at this temperature for 1.5h. TLC indicated complete consumption of 3-chloro-2-flurobenzyl bromide (sm: Rf=0.4; 30% EtOAc-hexanes). (0021) A solution of (3-chloro-2-fluorobenzyl)zinc bromide in THF (7.98mL, 7.98mmol, 1.0M) was added dropwise over a 10min period to a stirring mixture of 5-bromo-2-chloronicotinate (2.0g, 7.98mmol), tetrakis(triphenylphosphine)palladium (0.923g, 0.798mmol), and THF (26.6mL) at 65C. The resulting mixture was stirred for 1h and then poured into 10% aq. NH4Cl and the layers were separated. The aqueous phase was extracted with EtOAc and the combined organics layers were dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography (10-100% EtOAc-hexanes gradient) to yield the title compound as a yellow oil. (1.8g, 71.8%): 1H NMR (400MHz, CDCl3) delta ppm 8.41 (d, J=2.38Hz, 1H), 7.97 (d, J=2.38Hz, 1H), 7.37-7.29 (m, 1H), 7.08-7.04 (m, 3H), 4.04 (s, 2H), 3.97-3.92 (m, 3H); ES+ MS: 315 (M+1).
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Reference:
Article; Velthuisen, Emile J.; Johns, Brian A.; Temelkoff, David P.; Brown, Kevin W.; Danehower, Susan C.; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 99 – 112;,
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