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.1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid, molecular formula is C7H6BrNO3, molecular weight is 232.0314, as common compound, the synthetic route is as follows.Safety of 5-Bromo-6-methoxypicolinic acid
A solution of 5-bromo-6-methoxypicolinic acid (3.24 g, 14.0 mmol, 1.1 equiv.) in DCM (63.5 mL) at ambient temperature was treated with a catalytic amount of DMF (7 drops) and oxalyl chloride (3.32 mL, 38.1 mmol, 3.0 equiv.). The resultant mixture was stirred at ambient temperature for 1 h at which point LCMS monitoring showed completion of the reaction. The mixture was concentrated, diluted with anhydrous THF (40.0 mL), concentrated again before being dried under high vacuum for 1 hour. The residue was diluted in anhydrous THF (40.0 ml), treated with triethylamine (6.18 mL, 44.4 mmol, 3.5 equiv.) and cooled toO C. A solution of(R)-2-(4-methoxybenzylamino)-2-(4- methylbenzofuran-2-yl)ethanol (3.95 g, 12.7 mmol, 1.0 equiv.) in THF (45.0 ml) was then quickly added and the resultant mixture was stirred at 0 C for 1 h. Volatiles were removed under vacuum and MeOH (80.0 mL) was added, followed by K2C03 (1.75 g, 12.7 mmol, 1.0 equiv.). The reaction mixture was stirred at ambient temperature for 16 hours before water and EtOAc were successively added, layers were separated, and the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by normal phase chromatography on silica (10- 50% EtOAc / hexanes) to afford the amide (4.58 g, 69%) as white foam. LCMS (ES+) [M+Hj+: 525.1/526.9.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214334-70-9, 5-Bromo-6-methoxypicolinic acid, and friends who are interested can also refer to it.
Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); A1;,
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