Sodium Bicarbonate → HCID 89782936, compound

Participants

Reaction Conditions

Reaction Steps

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (40 mg, 0.128 mmol), 5-bromo-N-(2-hydroxyethyl)pyridine-2-sulfonamide (43.2 mg, 0.154 mmol), PdCl2(dppf) (9.38 mg, 0.013 mmol), sodium bicarbonate (0.274 mL, 0.513 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 25-50% 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 (16.4 mg, 25.6%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.05 (q, J=6.48 Hz, 2H), 3.40-3.46 (m, 7H), 7.70 (d, J=1.01 Hz, 1H), 7.96 (t, J=5.81 Hz, 1H), 8.08 (dd, J=8.21, 0.88 Hz, 2H), 8.45 (s, 1H), 8.51 (dd, J=8.21, 2.40 Hz, 1H), 9.15 (dd, J=2.27, 1.01 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C15H13F3N4O3S, 387.1. found 387.2.

Provenance & Evidence