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.754230-78-9, name is 3-(Benzyloxy)-5-bromopyridin-2-amine, molecular formula is C12H11BrN2O, molecular weight is 279.13, as common compound, the synthetic route is as follows.category: pyridine-derivatives
To a solution of 3-benzyloxy-5-bronio-pyridin-2-ylamine (278 mg, 1.00 mmol) in propionitrile (24 mL) and DMF (6 mL) were added iV-methyl-7^-(3-methyl-benzofuran-2- ylmethyl)acrylamide ( 252 mg, 1.10 mmol), (/-Pr)2EtN (0.35 mL, 2.00 mmol), Pd(OAc)2 (22 mg, 0.10 mmol) and P(o-tol)3 (61 mg, 0.20 mmol), and the mixture was de-oxygenated with argon for 15 min. The mixture was heated to reflux overnight, allowed to cool, filtered through a pad of diatomaceous earth, and the filtrate was concentrated. Purification by column chromatography (silica gel, CH2Cl2ZMeOH, 96:4) and then by slow precipitation fromCH?Cfe/hexanes gave the title compound (165 mg, 39%) as a pale yellow solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-^5) delta 7.77 (s, IH), 7.58-6.94 (m, 12H), 6.27 (s, 2H), 5.19 (s, 2H), 5.00-4.78′ (ms 2H), 3.18-2.92 (m, 3H), 2.27 (s, 3H); MS (ESI) m/e 428 (M + H)+.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,754230-78-9, 3-(Benzyloxy)-5-bromopyridin-2-amine, and friends who are interested can also refer to it.
Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/67416; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem