Sodium Bicarbonate → HCID 89783119, compound

Participants

Reaction Conditions

Reaction Steps

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (58.3 mg, 0.187 mmol), 2-(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)-N-isopropylacetamide (77 mg, 0.28 mmol), PdCl2(dppf) (13.66 mg, 0.019 mmol), sodium bicarbonate (0.399 mL, 0.747 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 45 minutes in a microwave reactor. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 35-55% 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 (10.2 mg, 11.1%). 1H NMR (400 MHz, CD3OD) δ ppm 1.20 (d, J=6.57 Hz, 6H), 2.15 (s, 3H), 2.19 (s, 3H), 2.66 (s, 1H), 7.23 (s, 1H), 7.87 (s, 1H), 8.00 (d, J=1.01 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C18H20F3N5O, 380.2. found 380.3.

Provenance & Evidence