Reference of 220227-21-4, A common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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.
General procedure: To a solution of A/-(2,4-dimethoxybenzyl)-3-methyl-1 ,2,4-thiadiazol-5- amine (1.14 g, 4.30 mmol) in tetrahydrofuran (20 mL) was added lithium N’s(trimethylsilyl)amide (1 M solution in tetrahydrofuran, 4.3 mL, 4.3 mmol) at -78 C. The reaction mixture was stirred for 30 minutes at 0 C and a solution of 2,4,5- trifluorobenzenesulfonyl chloride (0.99 g, 4.30 mmol) in tetrahydrofuran (10 mL) was added dropwise at -78 C. After the addition was complete, the cooling bath was removed. The reaction mixture was stirred for 3 h at ambient temperature and saturated aqueous ammonium chloride (10 mL) was added. The mixture was extracted with ethyl acetate (2 x 30 mL). The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford A/-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-A/-(3-methyl- 1 ,2,4-thiadiazol-5-y)benzenesulfonamide in 42% yield (0.83 g) as a colorless solid: MS (ES+) m/z 459.8 (M + 1).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; XENON PHARMACEUTICALS INC.; SUN, Shaoyi; ZENOVA, Alla, Yurevna; CHAFEEV, Mikhail; JIA, Qi; ZHANG, Zaihui; OBALLA, Renata, Marcella; WO2013/64983; (2013); A1;,
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