Reaktion #86376

Reaktionsgleichung

4-Bromo-6-(trifluoromethyl)-1H-indazole

(3-sulfamoylphenyl)boronic acid

sodium bicarbonate

→

title compound

Ausbeute 69.5%

3-(6-(trifluoromethyl)-1H-indazol-4-yl)benzenesulfonamide

Ausbeute 69.5%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give an orange suspension
2. 2
   SonstigeThe vial was sealed
3. 3
   FiltrationThe reaction mixture was subsequently filtered
4. 4
   Sonstigethe product was purified by preparative HPLC
5. 5
   Wascheneluting with a gradient of 35-70% ACN in H2O (containing 10 mM NH4HCO3)

Vorschrift

4-Bromo-6-(trifluoromethyl)-1H-indazole (40 mg, 0.151 mmol), (3-sulfamoylphenyl)boronic acid (45.5 mg, 0.226 mmol), PdCl2(dppf) (11.04 mg, 0.015 mmol), sodium bicarbonate (323 μL, 0.604 mmol), and dioxane were mixed in a 10 mL vial to give an orange suspension. The vial was sealed and then heated to 140° C. for 20 minutes in a microwave reactor. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 35-70% ACN in H2O (containing 10 mM NH4HCO3). The pure fractions were lyophilized to give the title compound as a white solid (35.8 mg, 69.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.50 (s, 2H), 7.53 (s, 1H), 7.75-7.80 (m, 1H), 7.92-7.94 (m, 1H), 8.02 (s, 1H), 8.06 (dt, J=8.02, 1.29 Hz, 1H), 8.21 (t, J=1.64 Hz, 1H), 8.40 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H10F3N3O2S, 342.0. found 342.2.

Quelle