Synthetic Route of 263349-73-1,Some common heterocyclic compound, 263349-73-1, name is 4-Bromo-3-fluorobenzenesulphonamide, molecular formula is C6H5BrFNO2S, 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.
A vessel was charged with 4-bromo-3-fluorobenzenesulfonamide (2, 255 mg, 1.00 mmol), Bis(pinacolato)diboron (280 mg, 1.10 mmol), Potassium acetate (295 mg, 3.01 mmol) and degassed dry 1,4-dioxane (5.02 mL). The vessel was evacuated and backfilled with argon (3x), XPhos Pd G4 (4.32 mg, 0.00502 mmol) was added and the mixture stirred at 85 C for overnight. After cooling to RT, the mixture was diluted with EtOAc and Acetic Acid (0.172 mL, 3.01 mmol), stirred for 30 minutes and filtered over Celite. The solvent was removed under reduced pressure. The residue was dissolved in a minimum amount of EtOAc, precipitated with n-heptane and the solids collected by suction filtration to yield 3-fluoro-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (220 mg, 0,7310 mmol, 73% yield) which was used without further purification. (0844) Analytical data: (0845) 1H NMR (200 MHz, DMSO) delta 7.91- 7.09 (m, 5H), 1.42- 0.95 (m, 12H); (0846) 13C NMR (50 MHz, DMSO) delta 148.6 (d, J = 8.2 Hz), 137.5 (d, J = 8.3 Hz), 121.05 (d, J = 2.1 Hz), 112.48 (d, J = 27.6 Hz), 83.9, 73.6, 25.0, 24.7.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-fluorobenzenesulphonamide, its application will become more common.
Reference:
Patent; HEPAREGENIX GMBH; PRAEFKE, Bent; KLOeVEKORN, Philip; SELIG, Roland; ALBRECHT, Wolfgang; LAUFER, Stefan; (157 pag.)WO2019/149738; (2019); A1;,
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