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.
To a stirred solution of 2,6-bis(benzyloxy)-3-bromopyridine (16-1) (177 mg, 480 mumol), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 24-1 (100.0 mg, 480 mumol) and potassium phosphate (221 mg, 960 mumol) in water: dioxane (10 mL) was degassed with argon for 10 minute. PdCl2(dppf)-DCM (39.1 mg, 48.0 mumol) was added to above reaction mixture and the solution was again purged with argon and refluxed for 16 hour at 100C. After completion of the reaction was observed by TLC ( Rf = 0.5 in 30% EtOH/Hexane), the reaction mixture was filtered through celite and concentrated. The residue was again dissolved in EtOAc (50 mL), washed with water, brine and evaporated. The crude residue was purified by combi flash chromatography (4 g Isco gold, hexane/EtOAc 70-30%) to give 2,6-bis(benzyloxy)-3-(1-methyl- 1H-pyrazol-3-yl)pyridine 24-2 (120 mg, 323 mumol, 67.4 %) as a white gummy solid. 1H NMR (400 MHz, DMSO-d6) delta 8.17 (d, J = 8.2 Hz, 1H), 7.65 (d, J = 1.9 Hz, 1H), 7.46-7.42 (m, 4H), 7.39-7.33 (m, 4H), 7.33-7.31 (m, 2H), 6.61 (d, J = 2.1 Hz, 1H), 6.51-6.49 (m, 1H), 5.46 (s, 2H), 5.37 (s, 2H), 3.85 (s, 3H). Synthesis
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;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem