Application of 363-51-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 363-51-9, name is 2-Chloro-6-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
To a 0 C stirred solution of 5-fluoro-4-(3-oxo-5,6 -dihydro-3H-[1 ,2,4]triazolo[3,4-c][1 ,4]oxazin- 2(8H)-yl)-2-{[(2S)-1 ,1 ,1 -trifluoropropan-2-yl]oxy}benzoic acid (intermediate 24) (74.3 mg, 190 muiotaetaomicronIota) and DMF (3 drops) in anhydrous dichloromethane (0.95 ml) was added oxalyl chloride dropwise (28,9 mg, 0.23 mmol). The resulting mixture was warmed to room temperature, stirred for one hour and concentrated under reduced pressure. A solution of the crude acid chloride in dichloromethane (0.63 ml) was then added dropwise to a 0 C stirred solution of 2- chloro-6-fluoraniline (30.4 mg, 0.21 mmol) and triethylamine (21 .1 mg, 0.21 mmol) in dichloromethane (0.70 ml). Following complete addition, the mixture was warmed to room temperature and stirred for one hour. Aqueous hydrochloric acid (1 .0 M, 10 ml) was added to the residue and extracted with dichloromethane (3 x 10 ml). The combined organic extracts were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a pale yellow oil. The residue was purified by reverse phase column chromatography (acetonitrile, 0.1 % aqueous formic acid) to give the amide as a white solid (73.3 mg, 66 %).LC-MS (method A): Rt = 1 .18 min; MS (ESIpos): m/z = 519 [M+H]+1H-NMR (400 MHz, CHLOROFORM-d) delta [ppm]: 1 .572 (8.35), 1 .659 (7.01 ), 1.676 (7.05), 3.807 (2.84), 3.820 (4.22), 3.834 (3.51 ), 4.086 (3.74), 4.098 (3.02), 4.100 (4.34), 4.1 13 (2.89), 4.772 (16.00), 4.91 1 (0.46), 4.927 (1 .09), 4.942 (1 .41 ), 4.958 (1 .09), 4.973 (0.42), 7.1 12 (0.89), 7.1 16 (0.94), 7.133 (1 .48), 7.136 (1 .96), 7.140 (1 .10), 7.155 (1.20), 7.159 (1 .25), 7.222 (0.85), 7.235 (0.84), 7.242 (1 .98), 7.256 (2.1 1 ), 7.263 (2.04), 7.285 (2.13), 7.290 (2.75), 7.305 (0.88), 7.309 (1 .07), 7.312 (0.89), 7.463 (2.95), 7.477 (2.96), 8.182 (3.04), 8.212 (3.06), 9.021 (2.04).
The synthetic route of 2-Chloro-6-fluoroaniline has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE GENERAL HOSPITAL CORPORATION; GRADL, Stefan, Nikolaus; NGUYEN, Duy; EIS, Knut; GUENTHER, Judith; STELLFELD, Timo; JANZER, Andreas; CHRISTIAN, Sven; MUELLER, Thomas; EL SHEIKH, Sherif; ZHOU, Han, Jie; ZHAO, Changjia; SYKES, David B; FERRARA, Steven, James; LIU, Kery; HERBERT, Simon, Anthony; MERZ, Claudia; NIEHUES, Michael; NISING, Carl, Friedrich; SCHAeFER, Martina; ZIMMERMANN, Katja; KNAEBLEIN, Joerg; THEDE, Kai; FAUPEL, Thomas; (539 pag.)WO2018/77944; (2018); A2;,
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