Sodium Bicarbonate → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole, (S)-5-((4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)methyl)pyrrolidin-2-one, PdCl2(dppf), sodium bicarbonate, 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 (8 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.98 (s, 3H), 2.10 (s, 3H), 2.16 (s, 3H), 4.09 (d, J=5.31 Hz, 2H), 7.16 (s, 1H), 7.81 (s, 1H), 7.86 (s, 1H), 8.03 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C18H18F3N5O, 378.1. found 378.3.

Provenance & Evidence