Application of 337915-79-4,Some common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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: HATU (4.89 g, 12.9 mmol) was added to a solution of the intermediate 4-bromo-N2-ethylbenzene-1,2-diamine, DIPEA (6.40 mL, 36.7 mmol), and cyclopropanecarboxylic acid (0.98 mL, 12.2 mmol) in DMF (40 mL), and the mixture was stirred at rt for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was dissolved in AcOH (40 mL) and the mixture was stirred at 80 C for 1 h. After concentration of the mixture, the residue was neutralized with satd NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexane/EtOAc = 100/0 to 0/100) to give the title compound (1.2 g, 37%) as a pale yellow solid.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-N1-methylbenzene-1,2-diamine, its application will become more common.
Reference:
Article; Igawa, Hideyuki; Takahashi, Masashi; Shirasaki, Mikio; Kakegawa, Keiko; Kina, Asato; Ikoma, Minoru; Aida, Jumpei; Yasuma, Tsuneo; Okuda, Shoki; Kawata, Yayoi; Noguchi, Toshihiro; Yamamoto, Syunsuke; Fujioka, Yasushi; Kundu, Mrinalkanti; Khamrai, Uttam; Nakayama, Masaharu; Nagisa, Yasutaka; Kasai, Shizuo; Maekawa, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 24; 11; (2016); p. 2486 – 2503;,
Bromide – Wikipedia,
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