Category: 263349-73-1

Electric Literature of 263349-73-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 263349-73-1 as follows.

EXAMPLE 342: 3-fluoro-4-(6-(trifluoromethyl)-lH-indazol-4- yl)benzenesulfonamide [0976] To a 5 mL vial equipped with a magnetic stir bar were added 4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-lH-indazole (40 mg, 0.128 mmol), 4-bromo-3- fluorobenzenesulfonamide (39.1 mg, 0.154 mmol), aqueous saturated sodium bicarbonate (0.274 mL, 0.513 mmol), PdCl2(dppf) (9.38 mg, 0.013 mmol), and dioxane (2 mL) to give an orange suspension. The vial was sealed and then heated in a microwave reactor at 140C for 30 minutes. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 35-60% ACN (containing 0.035% TFA) in H20 (containing 0.05% TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a white solid (13.7 mg, 22.6%). 1H NMR (400 MHz, DMSO-<) delta ppm 7.50 (s, 2 H), 7.53 (s, 1 H), 7.75-7.80 (m, 1 H), 7.92-7.94 (m, 1 H), 8.02 (s, 1 H), 8.06 (dt, J=8.02, 1.29 Hz, 1H), 8.21 (t, J=1.64 Hz, 1 H), 8.40 (s, 1 H); ESI-MS m/z [M+H]+ calc'd for Ci4H9F4N302S, 360.0; found 360.1. According to the analysis of related databases, 263349-73-1, the application of this compound in the production field has become more and more popular. Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; ERICKSON, Philip; FENG, Jun; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; MIURA, Joanne; MURPHY, Sean; TANG, Mingnam; TON-NU, Huong-Thu; WO2013/130855; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 263349-73-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 263349-73-1 as follows.

EXAMPLE 342: 3-fluoro-4-(6-(trifluoromethyl)-lH-indazol-4- yl)benzenesulfonamide [0976] To a 5 mL vial equipped with a magnetic stir bar were added 4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-lH-indazole (40 mg, 0.128 mmol), 4-bromo-3- fluorobenzenesulfonamide (39.1 mg, 0.154 mmol), aqueous saturated sodium bicarbonate (0.274 mL, 0.513 mmol), PdCl2(dppf) (9.38 mg, 0.013 mmol), and dioxane (2 mL) to give an orange suspension. The vial was sealed and then heated in a microwave reactor at 140C for 30 minutes. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 35-60% ACN (containing 0.035% TFA) in H20 (containing 0.05% TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a white solid (13.7 mg, 22.6%). 1H NMR (400 MHz, DMSO-<) delta ppm 7.50 (s, 2 H), 7.53 (s, 1 H), 7.75-7.80 (m, 1 H), 7.92-7.94 (m, 1 H), 8.02 (s, 1 H), 8.06 (dt, J=8.02, 1.29 Hz, 1H), 8.21 (t, J=1.64 Hz, 1 H), 8.40 (s, 1 H); ESI-MS m/z [M+H]+ calc'd for Ci4H9F4N302S, 360.0; found 360.1. According to the analysis of related databases, 263349-73-1, the application of this compound in the production field has become more and more popular. Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; ERICKSON, Philip; FENG, Jun; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; MIURA, Joanne; MURPHY, Sean; TANG, Mingnam; TON-NU, Huong-Thu; WO2013/130855; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics