The synthetic route of 32601-86-8 has been constantly updated, and we look forward to future research findings.
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.
General procedure: A mixture of azine chloride (0.50 mmol), Pd(PPh3)2Cl2 (42 mg, 0.06 mmol), CuI (6 mg, 0.03 mmol) and Et3N (6 mL) was stirred under argon for 20 min at room temperature. Then a solution of ethynyltrimethylsilane (63 mg, 0.09 mL, 0.64 mmol) was added dropwise. The flask was closed tightly. The resulting mixture was stirred for 24 h at 50-55C. The reaction mixture was evaporated to dryness without heating. The residue was mixed with silica gel and purified by flash column chromatography on silica gel (3¡Á30cm) with CHCl3 as the eluent. We were unable to obtain by chromatography pure samples of (trimethylsilyl)ethynyl derivatives because of their partial desilylation. Thus, pure (trimethylsilyl)ethynyl derivatives or partially desilylated products were subjected to desilylation according to the following procedure. To a solution of (trimethylsilyl)ethynyl azine (0.5 mmol) in methanol (5 mL), KF*2H2O (56 mg, 0.6mmol) was added. The reaction mixture was stirred for 24 h at room temperature and then evaporated to dryness. The residue was purified by flash column chromatography on silica gel with CH2Cl2 as the eluent. Rf, yield and characteristics for each compound are given below. All alkynes decompose when stored. 2-Methyl-3-((trimethylsilyl)ethynyl)quinoxaline Rf 0.3, 38%. Brown solid with mp 45-48C; 1H NMR (CDCl3) delta ppm: 0.35 (s, 9H), 2.89 (s, 3H), 7.68-7.75 (m, 2H), 7.99 (dd, J=7.7, 1.8Hz, 1H), 8.05 (dd, J=7.7, 1.8Hz, 1H); 13C NMR (CDCl3) delta ppm:-0.4, 23.2, 101.6, 102.5, 128.4, 128.9, 129.5, 130.5, 139.3, 140.6, 140.7, 155.3; IR, cm-1: 2161 (?C); MS (ESI) m/z: found 241.1163 [M+H]+, calcd for C14H16N2Si 241.1156 [M+H]+. 2-Ethynyl-3-methylquinoxaline (1b) Rf 0.4, 89%. Brown solid with mp 97-99C; 1H NMR (CDCl3) delta ppm: 2.90 (s, 3H), 3.58 (s, 1H), 7.70-7.77 (m, 2H), 8.00 (dd, J=7.9, 1.5Hz, 1H), 8.05 (dd, J=7.9, 1.5Hz, 1H); 13C NMR (CDCl3) delta ppm: 23.1, 80.9, 83.2, 128.5, 128.9, 129.6, 130.8, 138.6, 140.7, 140.9, 155.2; IR, cm-1: 2098 (?C); MS (ESI) m/z: found 169.0767 [M+H]+, calcd for C11H8N2 169.0760 [M+H]+., 32601-86-8
The synthetic route of 32601-86-8 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Nelina-Nemtseva, Julia I.; Gulevskaya, Anna V.; Suslonov, Vitaliy V.; Misharev, Alexander D.; Tetrahedron; vol. 74; 10; (2018); p. 1101 – 1109;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider