Electric Literature of 13466-35-8 ,Some common heterocyclic compound, 13466-35-8, molecular formula is C5H4ClNO, 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.
To a stirred solution of triphenylphosphine (814 mg, 3.10 mmol) in THF (7 ml) was added DIAD (603 mul, 3.10 mmol) at 0 oC. The mixture was stirred at 0 oC for about 10 min. To this mixture were added 3-chloro-2-hydroxypyridine (321 mg, 2.481 mmol) and tert- butyl 7-hydroxy-4-azaspiro[2.5]octane-4-carboxylate (470 mg, 2.068 mmol). The mixture was slowly warmed up to RT and stirred at RT overnight. The reaction was quenched with the addition of MeOH (~ 2 ml), and the mixture was concentrated and purified by Isco CombiFlash system on silica gel column (ISCO RediSep gold column, 80g) using 0-100%EtOAc/hexane to give the title compound as an oil after concentration. LCMS m/z [M+H]+ 283.13.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 13466-35-8, 3-Chloro-2-hydroxypyridine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; MERCK SHARP & DOHME CORP.; CLAUSEN, Dane; FRADERA, Xavier; GUO, Liangqin; HAN, Yongxin; HE, Shuwen; HUANG, Xianhai; KOZLOWSKI, Joseph; LI, Guoqing; LIM, Jongwon; MARTINOT, Theodore, A.; PASTERNAK, Alexander; SCIAMMETTA, Nunzio; VERRAS, Andreas; XIAO, Li; YU, Wensheng; ZHANG, Rui; (146 pag.)WO2020/41100; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem