Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 139585-48-1, name is 2-Chloro-5-methoxypyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6ClNO
A solution of 5-(tributylstannyl)thiazole (295 mg, 0.788 mmol) and 2-chloro-5-methoxypyridine (75 mg, 0.526 mmol) in toluene (2.0 mL) was degassed with argon for 3 min. Pd(PPh3)4 (24.29 mg, 0.021 mmol) was added. The reaction mixture was sealed and heated in an oil bath at 105 C for 4 h. After being cooled to room temperature, the reaction mixture was directly loaded on a column for purification. The crude product was purified by flash chromatography (loading in chloroform, 0% to 85% EtOAc in hexane over 10 min using a 4 g silica gel cartridge). The desired fractions were combined and concentrated to yield Intermediate 52A (70 mg, 0.364 mmol, 69.3 % yield) as a white solid.1H NMR (400MHz, METHANOL-d4) delta 8.94 (s, 1H), 8.26 (s, 1H), 8.19 (d, J=2.9 Hz, 1H), 7.75 (d, J=8.6 Hz, 1H), 7.36 (did, J=8.7, 3.0 Hz, 1H), 3.88 (s, 3H); LC^MS: method C, RT = 0.64 min, MS (ESI) m/z: 193.3 (M+H)+.
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Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy M.; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; (111 pag.)WO2018/13772; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem