With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.887590-25-2,tert-Butyl 3,4-dihydroquinoxaline-1(2H)-carboxylate,as a common compound, the synthetic route is as follows.
887590-25-2, To a round bottom flask charged with compound 14-2 (90mg, 0.38 mmol) and methyl 4-(bromomethyl)benzoate (87 mg, 0.38 mmol) in DMF (5 mL) was added K2CO3 (105 mg, 0.76 mmol). The resulting mixture was allowed to stir for 2 h at 80 C. The mixture was cooled to room temperature and after addition of water (15 mL) extracted with EtOAc (3 x 15 mL). The combined organic extracts were washed with brine (20 mL), dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by flash chromatography (0 – 5% MeOH/DCM), and the title compound was obtained as an off- white waxy solid (90 mg, 60%).1H NMR (CDCI3) delta 7.99, 7.32 (AlphaAlpha’ChiChi’ multiplet, AX + /AX’ = 8.2 Hz, 4H), 7.48 (br d, / = 7.4 Hz, 1H), 7.32 (d, / = 7.9 Hz, 2H), 6.90 (incompletely resolved ddd approaching dt, average of two larger / = 7.8 Hz, additional / = 1.1 Hz, 1H), 6.66 (incompletely resolved ddd approaching dt, average of two larger / = 7.6 Hz, additional / = 1.2 Hz, 1H), 6.55 (dd, / = 8.2 Hz, 0.9 Hz, 1H), 4.56 (s, 2H), 3.90 (s, 3H), 3.86, 3.44 (AA’XX’ multiplet, AX + /AX’ = 10.2 Hz, 4H), 1.53 (s, 9H). 13C NMR (DMSO- 6) delta 166.9, 153.3, 143.7, 138.2, 130.1 (2C), 129.1, 126.5 (2C), 125.1, 124.7, 116.3, 111.6, 100.0, 81.1, 54.9, 52.1, 49.5, 41.6, 28.4 (3C). ESI LRMS: [M+H]+, mlz 383.3.
As the paragraph descriping shows that 887590-25-2 is playing an increasingly important role.
Reference£º
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; KOZIKOWSKI, Alan; SHEN, Sida; BERGMAN, Joel; (100 pag.)WO2017/142883; (2017); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider