Synthetic Route of 13466-38-1 , The common heterocyclic compound, 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
4.43g (0.0200ml) of N-(4-fluorobenzyl)-1-oxa-6-azaspiro[2,5]-octane and 3.55g (0.0202mol) of 5-bromo-2-hydroxy- pyridine were weighed and added into 40mL of N,N-dimethylformamide, and then 0.15g (0.0011mol) of potassium carbonate was added. The reaction was stirred and reacted at a bath temperature of about 80C for 1 day and the solvent was recovered under reduced pressure. Potassium carbonate aqueous solution was added to the residue and the mixture was extracted with dichloromethane twice, combined, washed with water and dried, and the solvent was recovered. The residue was crystallized with petroleum ether-ethyl acetate to obtain a colorless flake-like crystal, 2.65g, yield 33.2%. Melting point: 181-183C. 1H-NMR (CDCl3, ppm) delta: 7.419 (1H, s), 7.405 (1H, dd, J1 = 9.80 Hz, J2 = 2.52 Hz), 7.252 (1H, t, J = 8.68 Hz), 6.990 (2H, t, J = 8.68 Hz), 6.547 (1H, d, J = 9.80 Hz,), 4.000 (2H, s), 3.864 (1H, s), 3.480 (2H, s), 2.641 (2H, dd, J1 = 7.84 Hz, J2 = 3.92 Hz), 2.352 (2H, t3d, J1 = 9.84 Hz, J2 = 1.96 Hz), 1.53-1.73 (4H, m). 2.65g of free base was weighed, heated and dissolved in ethanol-ethyl acetate, salified with HCl-EtOH while warm and naturally cooled to obtain a colorless fine granular crystal, which was dried under vacuum to obtain 2.29g product. Melting point: 255-257C, yield: 80%.
The synthetic route of 13466-38-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China; LI, Yunfeng; YANG, Rifang; ZHANG, Youzhi; LI, Yongzhen; JIN, Zengling; LI, Peng; YUAN, Li; YUN, Liuhong; ZHAO, Nan; ZHANG, Cheng; XU, Xiaodan; ZHAO, Rusheng; CHEN, Hongxia; XUE, Rui; QIN, Juanjuan; WANG, Zhenzhen; YAO, Jiazhi; EP2570410; (2013); A1;,
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