With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-02-0,6-Bromo-2-chloroquinoxaline,as a common compound, the synthetic route is as follows.
A slurry of 5-cyclopropyl-3-(2,6-dichlorophenyl)-4-(7-azaspiro[3.5]non-1-en-2-yl)isoxazole (25 mg, 0.07 mmol, synthesis described in General Method A), 6-bromo-2-chloroquinoxaline (19.5 mg, 0.08 mmol) and Cs2CO3 (43.4 mg, 0.13 mmol) in dioxane (0.3 mL) was degassed by bubbling nitrogen through the mixture for 5 minutes. Chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (RuPhos-Pd-G2) (2.59 mg, 3.33 mumol) was added and the reaction mixture was sealed and heated to 90C. for 6 hours. The crude reaction mixture purified directly by flash chromatography on SiO2 (0-100% EtOAc/hexanes, Isco 12 g column) to yield 4-(7-(6-bromoquinoxalin-2-yl)-7-azaspiro[3.5]non-1-en-2-yl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole (26 mg, 0.04 mmol, 64% yield) as a gum. 1H NMR (400 MHz, CDCl3) delta 8.57 (s, 1H), 8.03 (d, J=2.2 Hz, 1H), 7.64 (dd, J=8.8, 2.2 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.46-7.42 (m, 2H), 7.40-7.34 (m, 1H), 5.80 (s, 1H), 3.94 (dt, J=13.5, 5.1Hz, 2H), 3.66-3.50 (m, 2H), 2.44 (s, 2H), 2.21 (tt, J=8.4, 5.1Hz, 1H), 1.76 (t, J=5.6 Hz, 4H), 1.36-1.30 (m, 2H), 1.22-1.15 (m, 2H)., 55687-02-0
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Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; Carpenter, Joseph E.; Huang, Yanting; Wang, Ying; Wu, Gang; (137 pag.)US2019/127362; (2019); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider