Sodium Carbonate → 4(2,4-dimethoxypyrimidin-5-yl)-6-(trifluoromethyl)-1H-indazole

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Reaction Conditions

Reaction Steps

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (100 mg, 0.320 mmol), 5-iodo-2,4-dimethoxypyrimidine (57 mg, 0.215 mmol), and PdCl2(dppf) (23 mg, 0.032 mmol) were dispersed in dioxane (3 mL). To the resulting slurry was added 2N aqueous sodium carbonate (0.320 mL, 0.641 mmol). The mixture was heated in a microwave reactor at 130° C. for 1 hour, and then filtered through a microfiltration frit, which was rinsed with methanol. The solvents were removed in vacuo and the resulting residue was taken up in DMSO and methanol (1:1) and was purified via preparative HPLC, eluting with a gradient of 40-45% ACN (containing 0.1% formic acid) in H2O (containing 0.1% formic acid). The purified fractions were collected to give a formic acid salt of the title compound (33.5 mg, 32.2%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.95 (s, 3H), 4.00 (s, 3 H), 7.43 (s, 1H), 7.95 (s, 1H), 8.12 (s, 1H), 8.52 (s, 1H), 13.64 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H11F3N4O2, 325.1. found 325.2.

Provenance & Evidence