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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, A new synthetic method of this compound is introduced below., name: 3-Chloro-5-trifluoromethylaniline
[0092] Synthesis of trans-V-tert-buty 4′-ethyl 3-((3-chloro-5-(trifluoromethyl) phenyl)amino)-2-oxo-[l,3′-bipiperidine]- ,4′-dicarboxylate. A 1.0 M solution of lithium bis(trimethyldisilyl)amide in THF (13 mL, 12 mmol, 2.0 equiv) was added through an addition funnel at 10-15 C to a solution of 3-chloro-5-(trifluoromethyl)aniline (15 g, 78 mmol, 1.2 equiv) in THF (13 mL). The mixture was allowed to stir at room temperature for 20 min and a solution of crude trans- -tert-butyl-4′-ethyl-3-iodo-2-oxo-[l,3′-bipiperidine]- ,4′- dicarboxylate 9 (3.7 g, 65 mmol, 1.0 equiv) in THF (13 mL) was added through an addition funnel at 10-15 C over 30 min. After addition, the reaction was allowed to stir at the temperature for 30 min. Upon completion, the reaction was cooled to 5 C and quenched slowly with water (10 mL), keeping the temperature below 20 C. The quenched reaction was extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with saturated brine (30 mL), dried (Na2S04), filtered, and concentrated in vacuo. The resulting crude product was purified over silica gel eluting with a gradient of 10% to 75%> of EtOAc in heptanes to give the desire product 10. ESI- MS (M+H-56) +: 463.1. 1H NMR (400 MHz, CDC13) delta: 6.92 (s, 1H), 6.71-6.69 (m, 2H), 4.17- 4.06 (m, 4H), 3.78-3.68 (m, 2H), 3.46-3.36 (m, 3H), 3.23-3.07 (m, 2H), 2.73-2.65 (m, 1H), 2.44- 2.37 (m, 1H), 2.03-1.85 (m, 3H), 1.71-1.61 (m, 2H), 1.46 (s, 9H), 1.27-1.19 (m, 3H).
The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; CONLON, Patrick; CHAN, Timothy R.; JENKINS, Tracy J.; CAI, Xiongwei; HUMORA, Michael; SHI, Xianglin; MILLER, Ross A.; THOMPSON, Andrew; WO2013/185084; (2013); A1;,
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