Synthetic Route of 19230-55-8 , The common heterocyclic compound, 19230-55-8, name is 3-Chloro-5-methylpyridine, molecular formula is C6H6ClN, 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.
General procedure: 2 mol% Pd(OAc)2/3 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 45 C under an argon atmosphere for 1h to be a dark brown solution. 1 mol% CuI/1.1 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 60 C under an argon atmosphere for 2h to be a colorless transparent solution. The amount of catalyst and solvent should scaled up by the number of reactions. Benzoxazoles (0.25 mmol), aryl chlorides (0.3 mmol) and K3PO4*7H2O (42.3 mg, 0.125 mmol, 0.5 equiv) were added to an oven-dried 10 ml reaction vial equipped with a stir bar. A stock solution of Pd(OAc)2/Nixantphos and CuI/Nixantphos in 1 ml of dry DMF was taken up by syringe and added to the reaction vial. The reaction vial filled with argon was then sealed with a septum. The reaction mixture was stirred for12 h or 24 h at 120 C, quenched with two drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of MgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solution was concentrated in vacuo. The crude material was loaded onto a silica gel column and purified by flash chromatography.
The synthetic route of 19230-55-8 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Zheng, Ling-Li; Yin, Bo; Tian, Xing-Chuan; Yuan, Ming-Yong; Li, Xiao-Huan; Gao, Feng; Tetrahedron Letters; vol. 60; 51; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem