Methyl 5-iodo-6-oxo-1,6-dihydropyridine-3-carboxylate → methyl 6-oxo-5-(6-(trifluoromethyl)-1H-indazol-4-yl)-1,6-dihydropyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (43 mg, 0.138 mmol), methyl 5-iodo-6-oxo-1,6-dihydropyridine-3-carboxylate (38.4 mg, 0.138 mmol) and PdCl2(dppf) (5.04 mg, 6.89 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 solution (0.5 mL) was heated in a microwave reactor at 140° C. for 30 minutes. The reaction mixture was subsequently filtered and purified via preparative HPLC, eluting with a gradient of 20-90% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) to give the title compound as a white solid (7 mg, 15%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.19 (s, 1H), 8.09-8.14 (m, 2H), 7.94 (s, 1H), 7.62 (s, 1H), 3.82 (s, 3H); ESI-MS m/z [M+H]+ calc'd for C15H10F3N3O3, 338.1. found 338.2.

Provenance & Evidence