Synthetic Route of 16727-47-2, 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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine. A new synthetic method of this compound is introduced below.
A sealed tube was charged with 16-1 (1.0 g, 2.70 mmol), Et3N (4.89 mL, 35.1 mmol) and Ethynyltrimethylsilane (4.85 mL, 35.1 mmol) and the resulting solution was degassed with Argon for about 10 minutes followed by the addition of CuI (514 mg, 2.70 mmol) and PdCl2(PPh3)2 (1.89 g, 2.70 mmol). The reaction tube was sealed and heated at 90oC for 16 hours. The reaction was then cooled to room temperature and filtered through a short bed of celite. The filtrate was partitioned between heptane and water. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated. The crude mass was dissolved in MeOH (10 mL) and to it was added K2CO3 (713 mg, 5.16 mmol) and the solution was stirred at ambient temperature for 2 hours to produce 16-2. The reaction mass was filtered through a short bed of celite and the filtrate was concentrated under reduced pressure. The crude mass was purified by column chromatography (silica, gradient: 0-10% Ethyl acetate in Hexane) to afford 16-2 (462 mg, 1.46 mmol, 54%) as a white solid.1H NMR (400 MHz, DMSO-d6) delta 7.63 (d, J = 8.24 Hz, 1H), 7.43-7.28 (m, 10H), 7.34 (d, J = 8.16 Hz, 1H), 5.44 (s, 2H), 5.29 (s, 2H), 3.24 (s, 1H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,16727-47-2, 2,6-Bis(benzyloxy)-3-bromopyridine, and friends who are interested can also refer to it.
Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
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