Reference of 139585-48-1, 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.
To a 10 mL microwave tube was added sodium tert-butoxide (0.105 mL, 0.856 mmol), [dicyclohexyl(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine]2-(2-aminoethyl)phenyl)palladium(II) chloride (15.54 mg, 0.019 mmol), 2-chloro-5-methoxy-pyridine (61.5 mg, 0.428 mmol), 1-(trans-3-aminocyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (intermediate 26, 90 mg, 0.389 mmol) and dry dioxane (1 mL) and it was sealed under argon. The mixture was stirred at 110 C. for 2 hours. The vial was opened and the reaction mixture evaporated to dryness under reduced pressure. Purification using reverse phase HPLC gave 1-(trans-3-(bis(5-methoxypyridin-2-yl)amino)cyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (62 mg, 0.139 mmol, 35% yield). M+1: 446.1. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.35 (s, 6H) 2.47-2.61 (m, 2H) 3.20-3.33 (m, 2H) 3.83 (s, 6H) 4.97-5.14 (m, 1H) 5.20-5.33 (m, 1H) 6.83 (d, J=8.77 Hz, 2H) 6.92 (dd, j=7.16, 5.26 Hz, 1H) 7.17 (dd, J=8.84, 3.14 Hz, 2H) 7.39 (dd, J=7.16, 1.61 Hz, 1H) 8.10 (d, J=2.92 Hz, 2H) 8.17 (dd, J=5.26, 1.61 Hz, 1H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,139585-48-1, 2-Chloro-5-methoxypyridine, and friends who are interested can also refer to it.
Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem