Application of 706791-83-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 706791-83-5 name is Methyl 3-amino-5-bromobenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
To a solution of methyl 3-amino-5-bromobenzoate (61b, 219 mg, 0.950 mmol) in 1,4-dioxane (20 mL) were added bis(pinacolato)diboron (290 mg, 1.14 mmol), PdCl2(dppf) (23 mg, 28.5 pmol) and potassium acetate (279 mg, 2.85 mmol), and then this reaction mixture was stirred at 95 C for 15 h. The reaction mixture was partitioned ethyl acetate (20 mL) and water (10 mL), and the aqueous layer was extracted with ethyl acetate (10 mL x 2). The combined organic layer was washed brine (5 mL), dried over MgS04, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4: l) to afford compound 62 (180 mg, 68%) as a white solid; NMR (400 MHz, CDC13) d 7.88 (s, 1H), 7.46 (s, 1H), 7.31 (d, J =2.4 Hz, 1H), 3.91 (s, 3H), 1.36 (s, 12H); MS (ESI, m/z) 278.2 [M+l]+; ESI-HRMS calcd. m/z for (0572) Ci4H2iN04nB 278.1564, found 278.1565 [M+l]+.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromobenzoate, and friends who are interested can also refer to it.
Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; JACOBSON, Kenneth A.; YU, Jinha; CIANCETTA, Antonella; WEN, Zhiwei; JUNG, Young-Hwan; (124 pag.)WO2019/157417; (2019); A1;,
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