Water → N-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)pyrimidine-4-carboxamide

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 (0.144 g, 0.463 mmol), 5-bromo-N-methylpyrimidine-4-carboxamide (0.1 g, 0.463 mmol) and PdCl2(dppf) (0.017 g, 0.023 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 25-30% ACN in H2O (containing 10 mMol NH4HCO3) over a period of 8 minutes. The product-containing fractions were combined and the solvent was removed via rotary evaporation. The crude product was extracted into DCM and was washed with water. The volatiles were removed in vacuo to give the title compound as a white solid (0.018 g, 0.056 mmol, 12%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.62 (d, J=4.80 Hz, 3H), 7.43 (s, 1H), 8.04 (s, 1H), 8.01 (s, 1H), 8.89 (d, J=4.29 Hz, 1H), 9.09 (s, 1H), 9.38 (s, 1H), 13.72 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H10F3N5O, 322.1. found 322.2.

Provenance & Evidence