Electric Literature of 24036-52-0,Some common heterocyclic compound, 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, molecular formula is C8H6BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: Toluene (4.5mL) was added to a flask containing 6-bromo-3,4-dihydroquinolin-2(1H)-one (300mg, 1.33mmol), 3-(trifluoromethoxy)aniline (231muL, 1.73mmol), Pd2(dba)3 (15.2mg, 0.02mmol), 2-dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl (31.6mg, 0.07mmol) and NaOt-Bu (192mg, 2.00mmol) under an argon atmosphere. The mixture was stirred at 100C for 9h. After cooling, the reaction mixture was diluted with EtOAc, and filtered through a pad of Celite. The filtrate was concentrated in vacuo. Crude material was purified by flash chromatography with n-hexane/EtOAc (2:3) to afford the desired diaryl amine 11i
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, its application will become more common.
Reference:
Article; Takeuchi, Tomoki; Oishi, Shinya; Kaneda, Masato; Misu, Ryosuke; Ohno, Hiroaki; Sawada, Jun-Ichi; Asai, Akira; Nakamura, Shinya; Nakanishi, Isao; Fujii, Nobutaka; Bioorganic and Medicinal Chemistry; vol. 22; 12; (2014); p. 3171 – 3179;,
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