New downstream synthetic route of (2-Amino-5-bromophenyl)(pyridin-2-yl)methanone

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1563-56-0, its application will become more common.

Related Products of 1563-56-0, 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. 1563-56-0, name is (2-Amino-5-bromophenyl)(pyridin-2-yl)methanone. A new synthetic method of this compound is introduced below.

38.6 g (139 mmol) of (2-amino-5-bromophenyl)-pyridin-2-yl-methanone of formula (A) and 45.2 g (153 mmol) of (2S)-2- (benzyloxycarbonylamino) -5-methoxy-5-oxo-pentanoic acid were dissolved in 200 mL of dichloromethane at a temperature of about 15C. The solution was cooled at -10C, and a previously prepared solution containing 32.2 g (156 mmol) of N,N?dicyclohexylcarbodiimide in 65 mL of dichloromethane was slowlyadded at said temperature. The reaction mixture was kept under stirring at a temperature of about -10C for 48 hours, and the salts resulting from the reaction were then filtered at a temperature of about 15C.The reaction solvent was removed by means of distillationwith a vacuum at the maximum temperature of 25C, and 250 mL ofmethyl-tert-butylether were added. The obtained mixture was heated at 50C and then slowly cooled at a temperature of about 25C. The resulting solid was filtered and oven-dried at 50C.72.3 g (93.6%) of a very slightly yellowish solid correspondingto methyl (4S)-4-(benzyloxycarbonylamino)-5-[4-bromo-2-(pyridine-2-carbonyl)aniline]-5-oxo-pentanoate of formula (I-B)were thereby obtained. The purity of the obtained products wasanalyzed by means of the ultra high performance liquidchromatography technique in Waters Acquity HClass equipment,equipped with a variable wave detector and temperature-controlled oven for the column. Figure 2 shows the 1H-NMRspectrum. 1H-NMR (CDC13, 400 MHz) (ppm) : 11.43 (1H, s) , 8.73(1H, d) , 8.56 (1H, d) , 8 (1H, d) , 7.93 (1H, s) , 7.92 (1H, s)7.67 (1H, dd) , 7.52 (1H, m) , 7.35 (SH, m) , 5.71 (1H, d) , 5.04(2H, m), 4.45 (1H, m), 3.65 (3H, s), 2.50 (2H, m), 2.31 (1H, m),2.07 (1H, m)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1563-56-0, its application will become more common.

Reference:
Patent; MOEHS IBERICA, S.L.; SANCHEZ CASALS, Carles; DOBARRO RODRIGUEZ, Alicia; (66 pag.)WO2019/72944; (2019); A1;,
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