Sodium Bicarbonate → HCID 71736825, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (0.1 g, 0.320 mmol), (5-bromopyridin-2-yl)(morpholino)methanone (0.174 g, 0.641 mmol) and PdCl2(dppf) (0.012 g, 0.016 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light brown suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with a gradient of 35-45% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 5 minutes. The product-containing fractions were combined and the volatiles were removed in vacuo to give a TFA salt of the title compound as a light brown solid (0.053 g, 44%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.49-3.67 (m, 4H), 3.71 (s, 4H), 7.63 (s, 1H), 7.80 (dd, J=8.08, 0.76 Hz, 1H), 8.03 (s, 1H), 8.28-8.48 (m, 2H), 9.01 (dd, J=2.40, 0.88 Hz, 1H), 13.82 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H15F3N4O2, 377.1. found 377.

Provenance & Evidence