Sodium Bicarbonate → HCID 89783820, compound

Participants

Reaction Conditions

Reaction Steps

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (39.5 mg, 0.127 mmol), 5-bromopyridine-2-sulfonamide (45 mg, 0.190 mmol), PdCl2(dppf) (9.26 mg, 0.013 mmol), sodium bicarbonate (0.271 mL, 0.506 mmol), and dioxane (2 mL) 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 35-60% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a white solid (9.9 mg, 17%). 1H NMR (400 MHz, CD3OD) δ ppm 2.01 (s, 1H), 7.61 (d, J=1.26 Hz, 1H), 8.03 (s, 1H), 8.17-8.21 (m, 1H), 8.34 (d, J=1.01 Hz, 1H), 8.43 (dd, J=8.08, 2.27 Hz, 1H), 9.07 (dd, J=2.27, 0.76 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C13H9F3N4O2S, 343.0. found 343.2.

Provenance & Evidence