Reference of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, its 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.
Step-1: 2-Fluoro-5-nitrobenzonitrile (1.4g, 1.0 eq, 8.4 mmol) was taken in annhydrous DMF (10 mL). Secondary amine (1.2 eq, 10.12 mmol) was added to the above solution followed by the addition of K2C03 (3.5g, 3.0eq, 25.3 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted with EtOAc (100 mL) and partitioned with water (100 mL). Organic layers were separated and the aqueous layers were washed with EtOAc (1 x 50 mL). The combined oragnic layers were washed with aqueous staurated NaHC03 solution (100 mL) and dried over Na2S04. Organic layers were concentrated under reduced pressure to leave a crude mixture. The mixture was purified by column chromatography on silica gel (ISCO System) using EtOAc / Hexane (gradient system from 0: 1 to 2:8) as eluent to give the product as a solid. 2-(4-(Methylsulfonyl)piperazin-l-yl)-5-nitrobenzonitrile: Synthesized as described in Step-1. Yield = 73%, 1H NMR (300 MHz, CDC13) delta 8.43 (d, J = 2.1 Hz, 1H), 8.27 (dd, J = 9.3, 2.7 Hz, 1H), 6.98 (d, J = 9.3 Hz, 1H), 3.59 – 3.48 (m, 4H), 2.68 – 2.57 (m, 4H), 2.38 (s, 3H); LCMS (m z): 311 (M+H)+.
Statistics shows that 2-Fluoro-5-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 17417-09-3.
Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; SINGH, Rajinder; DUNCTON, Matthew; ZHANG, Jing; ALVAREZ, Salvador; TSO, Kin; HOLLAND, Sacha; YEN, Rose; KOLLURI, Rao; HECKRODT, Thilo; CHEN, Yan; MASUDA, Esteban; LI, Hui; PAYAN, Donald G.; KELLEY, Ryan; WO2013/152198; (2013); A1;,
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