New downstream synthetic route of 2-Amino-5-bromonicotinic acid

Application of 52833-94-0, 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.52833-94-0, name is 2-Amino-5-bromonicotinic acid, molecular formula is C6H5BrN2O2, molecular weight is 217.02, as common compound, the synthetic route is as follows.

Intermediate 16:2-amino-5-bromo-N-methoxy-N-methylnicotinamide[00400] To a solution of 2-amino-5-bromonicotinic acid (7 g, 32.3 mmol), N,0- dimethylhydroxylamine (5.99 g, 61.37 mmol) in N-methylmorpholine (60 ml) and dichloromethane (500 ml) at OC was added PyBop (25.2 g, 48.45 mmol) portionwise. The solution was allowed to warm to room temperature and the mixture was stirred at room temperature for 18 hours. The reaction mixture was washed with a 2M aqueous solution of NaOH and with a 10wt% solution of citric acid. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was dissolved in ether and the formed solid was filtered off. The mother liquors were concentrated in vacuo to approximatively half of the original volume. This solution was diluted with dichloromethane and stirred vigorously while adding a 2M HCl solution in diethylether until complete formation of the precipitate. The solid was filtered off and partitioned between a 2M aqueous solution of NaOH and EtOAc. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to dryness to afford the title compound as a cream solid (5.26 g, 63% yield). 1H NMR (DMSO-d6, 400 MHz) delta 3.24 (3H, s), 3.55 (3H, s), 6.35 (2H, s), 7.70 (IH, d), 8.10 (IH, d); MS (ES+) 260, 262.

Statistics shows that 52833-94-0 is playing an increasingly important role. we look forward to future research findings about 2-Amino-5-bromonicotinic acid.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/94992; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem