Sodium Bicarbonate → N,N-dimethyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.1 g, 0.377 mmol), N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.122 g, 0.491 mmol) and PdCl2(dppf) (0.014 g, 0.019 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 30-40% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 8 minutes. The product-containing fractions were combined and the volatiles removed in vacuo to give a TFA salt of the title compound as a light brown solid (68 mg, 59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.23 (s, 6H), 7.48 (d, J=1.01 Hz, 1H), 7.89 (s, 1H), 8.40 (d, J=0.76 Hz, 1H), 8.82 (s, 2H); ESI-MS m/z [M+H]+ calc'd for C14H12F3N5, 308.1. found 308.15.

Provenance & Evidence