1,4-Dioxane → HCID 89783083, 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-bromo-2-methoxypyrimidin-4-amine (0.131 g, 0.641 mmol) and PdCl2(dppf) (0.012 g, 0.016 mmol) in dioxane (8 mL) and aqueous saturated NaHCO3 (2 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 15-25% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 5 minutes. The product-containing fractions were combined and volatiles were removed in vacuo to give a TFA salt of the title compound as light brown solid (0.029 g, 29%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.04 (s, 3H), 7.35-7.41 (m, 1H), 8.03 (s, 1H), 8.06-8.15 (m, 1H), 8.21 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C13H10F3N5O, 310.1. found 310.13.

Provenance & Evidence