Some common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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. HPLC of Formula: C6H2ClF3O2S
A solution of ferf-butyl thiazol-4-ylcarbamate (3.46 g, 17.3 mmol) in tetrahydrofuran (150 mL) at -78 C was treated with lithium 6/’s(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 20.8 mL, 20.8 mmol). The resulting mixture was stirred at -78 C for 0.5 h, allowed to warm to ambient temperature and stirred for a further 0.5 h. The reaction mixture was cooled to -78 C and treated with a solution of 2,4,5- trifluorobenzene-1-sulfonyl chloride (3.99 g, 17.3 mmol) in tetrahydrofuran (30 mL). The resulting mixture was stirred at -78 C for 4 h, allowed to warm to ambient temperature and stirred for a further 16 h. The reaction mixture was diluted with ethyl acetate (300 mL) and washed with saturated aqueous ammonium chloride (2 x 150 mL) and brine (2 x 150 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a gradient of ethyl acetate in hexanes to afford terf-butyl thiazol-4-yl((2,4,5- trifluorophenyl)sulfonyl)carbamate as a beige solid in 62% yield (4.23 g): 1H NMR (300 MHz, CDCI3) 6 8.79-8.75 (m, 1 H), 8.06-7.96 (m, 1 H), 7.53-7.48 (m, 1H), 7.15-7.04 (m, 1 H), 1.34 (s, 9H); MS (ES+) m/z 394.7 (M + 1).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 220227-21-4, its application will become more common.
Reference:
Patent; XENON PHARMACEUTICALS INC.; LIU, Shifeng; FOCKEN, Thilo; CHAHAL, Navjot; ZHANG, Zaihui; OBALLA, Renata, Marcella; FONAREV, Julia; WO2013/64984; (2013); A1;,
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