Some common heterocyclic compound, 928782-97-2, name is 4-Chloro-2-(phenylethynyl)aniline, molecular formula is C14H10ClN, 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. name: 4-Chloro-2-(phenylethynyl)aniline
General procedure: The substituted 2-alkynylaniline (1.0 mmol) was dissolved in acetonitrile (5.0 mL) and stirred until the solution became homogeneous. To this solution, methyl vinyl ketone (1.5 mmol) followed by 20 mol % of PdCl2 (59-60%, 35 mg) was added under a nitrogen atmosphere, then heated to 60 C and monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and the acetonitrile was removed by vacuum evaporation. The resulting crude product was purified by column chromatography to afford the desired 2,3-disubstituted indoles. 1-(5-Chloro-2-phenyl-1H-indol-3-yl)pentan-3-one (3n) Yield: (300 mg, 96%); Colorless solid. Mp: 138-140 C. FT-IR (KBr) (nu/cm-1): 3370, 1711. 1H NMR (400 MHz, CDCl3) deltaH (ppm): 8.10 (br s, 1H), 7.55-7.53 (m, 3H), 7.47 (t, J=7.5 Hz, 2H), 7.40-7.36 (m, 1H), 7.27 (d, J=8.56 Hz, 1H), 7.15 (dd, J=8.5, 1.9 Hz, 1H), 3.15-3.11 (m, 2H), 2.77-2.73 (m, 2H), 2.39 (q, J=7.3 Hz, 2H), 1.03 (t, J=7.3 Hz, 3H). 13C NMR (100 MHz, CDCl3) deltaC (ppm): 211.1, 136.1, 134.4, 132.7, 130.1, 129.2, 128.3, 128.1, 125.5, 122.7, 118.6, 112.1, 111.9, 43.1, 36.2, 18.9, 7.9. LRMS (EI) (m/z) (relative intensity): 311 (M+, 50), 328 (100); HRMS calcd for C19H18Cl1O1N1 (M+): 311.1077, found 311.1086.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 928782-97-2, its application will become more common.
Reference:
Article; Janreddy, Donala; Kavala, Veerababurao; Kuo, Chun-Wei; Kuo, Ting-Shen; He, Chiu-Hui; Yao, Ching-Fa; Tetrahedron; vol. 69; 15; (2013); p. 3323 – 3330;,
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