HCID 89782899, compound → HCID 89782954, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial were added 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (0.993 g, 2.506 mmol), ethyl 4-bromo-3-methyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrazole-5-carboxylate (0.82 g, 2.506 mmol), and PdCl2(dppf) (0.092 g, 0.125 mmol) in dioxane (25 mL) and aqueous saturated NaHCO3 (6 mL). The mixture was bubbled with nitrogen to give a light yellow suspension, which was heated at 140° C. for 60 minutes in a microwave reactor. The reaction mixture was subsequently diluted with EtOAc, washed with water and brine, dried over Na2SO4, and concentrated. The crude residue was purified by CombiFlash® chromatography (120 g column) eluting with a gradient of 10-100% EtOAc in heptane over a period of 180 minutes. The product-containing fractions were combined and concentrated to give the title compound as an off white solid (0.745 g, 57.5%). ESI-MS m/z [M+H]+ calc'd for C25H27F3N6O3, 517.22. found 517.20.

Provenance & Evidence