The origin of a common compound about 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

The chemical industry reduces the impact on the environment during synthesis 99368-68-0, I believe this compound will play a more active role in future production and life.

Reference of 99368-68-0, 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.99368-68-0, name is 6-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.5576, as common compound, the synthetic route is as follows.

(0876) Under ice-cooling, thionyl chloride (4 ml) was added dropwise over 20 minutes to water (27 ml). The mixture was stirred overnight for 12 hours to give a SO2 containing solution. Separately, Compound 288C (1.14 g) in dioxane (5 ml) was added to concentrated HCl (20 ml) at 0 C. The solution was stirred for 5 minutes. To this suspension/solution was added sodium nitrite (0.44 g) in water (6 ml) dropwise at 0 C. The solution was stirred at 0 C. for 3 hours. During this time, any solid formed was crushed with a glass rod to make sure that Compound 288C was completely reacted. To the SO2 containing solution was added copper(I) chloride (0.115 g). Then, to this solution was added the diazotized Compound 288C at 0 C. The solution was stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with 5% ethyl acetate in hexanes to provide the title compound.

The chemical industry reduces the impact on the environment during synthesis 99368-68-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AbbVie Inc.; Catron, Nathaniel; Lindley, David; Miller, Jonathan M.; Schmitt, Eric A.; Tong, Ping; US10213433; (2019); B2;,
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