Sodium Bicarbonate → 4-(3,6-dimethoxypyridazin-4-yl)-6-(trifluoromethyl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.15 g, 0.566 mmol), (3,6-dimethoxypyridazin-4-yl)boronic acid (0.135 g, 0.736 mmol) and PdCl2(dppf) (0.021 g, 0.028 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 40-45% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6.5 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as a light brown solid (8 mg, 4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.97 (s, 3H), 4.03 (s, 3H), 7.42 (s, 1H), 7.55 (d, J=1.01 Hz, 1H), 8.05 (s, 1H), 8.14 (s, 1H), 13.74 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H11F3N4O2, 325.1. found 325.16.

Provenance & Evidence