Downstream synthetic route of 32601-86-8

32601-86-8 2-Chloro-3-methylquinoxaline 236276, aquinoxaline compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.32601-86-8,2-Chloro-3-methylquinoxaline,as a common compound, the synthetic route is as follows.

In a sealed tube and under an argon atmosphere were addedsuccessively, 2-chloro-3-methylquinoxaline (0.5 mmol), hydrazone3a (0.75 mmol) PdCl2(CH3CN)2 (10 mol%), [(tBu)2MePH]BF4 (20 mol%) in dry dioxane (4 mL) and the mixture was stirred for 5 min at rt.Then dry LiOtBu (1.8 mmol) was added and the mixture was stirredat 100 C for 3 h. The resulting suspension was cooled to roomtemperature, filtered through a pad of Celite eluting with ethylacetate and the inorganic salts were removed. The filtrate wasconcentrated and the crude was purified by silica gel columnchromatography.Beige solid, F 102.2-102.9 C. 1H NMR (300 MHz, CDCl3) delta 8.14(d, J 9.6 Hz, 1H), 8.05 (d, J 9.6 Hz, 1H), 7.84-7.62 (m, 2H), 7.20 (d,J 8.9 Hz, 2H), 6.85 (d, J 8.9 Hz, 2H), 5.93 (s, 1H), 5.46 (s, 1H), 3.80(s, 3H), 2.49 (s, 3H). 13C NMR (75 MHz, CDCl3) delta 159.9, 155.7, 153.5,147.1, 141.8, 136.6, 131.1, 129.9, 129.5, 129.3, 128.5, 127.8 (2), 116.2,114.2 (2), 55.4, 23.5. IR (neat) upsilonmax/cm-1: 2929, 2836, 1606, 1511,1440, 1248. HRMS calcd for C19H17N2O [M+H]+ 277.1341, obsd.277.1336., 32601-86-8

32601-86-8 2-Chloro-3-methylquinoxaline 236276, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Article; Khelifi, Ilhem; Naret, Timothee; Renko, Dolor; Hamze, Abdallah; Bernadat, Guillaume; Bignon, Jerome; Lenoir, Christine; Dubois, Joelle; Brion, Jean-Daniel; Provot, Olivier; Alami, Mouad; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 1025 – 1034;,
Quinoxaline – Wikipedia
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