Sodium Bicarbonate → methyl 1-isopropyl-3-methyl-6-(pyridin-3-yl)-1H-indazole-4-carboxylate

Participants

Reaction Steps

To a stirred solution of methyl 6-bromo-1-isopropyl-3-methyl-1H-indazole-4-carboxylate (0.5 g, 1.60 mmol) in 1,4-dioxane (25 mL) was added 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.39 g, 1.92 mmol) followed by PdCl2(dppf)-CH2Cl2 adduct (0.26 g, 0.32 mmol). The reaction mixture was stirred for 5 min, then sodium bicarbonate (0.4 g, 4.80 mmol) dissolved in water (8 mL) was added and the reaction mixture was stirred at 100° C. for 6 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with cold water (2×25 mL), brine solution (25 mL), dried over anhydrous Na2SO4, filtered, and concentrated to afford the crude product. The crude compound was purified by silica gel chromatography (eluent: 100% ethyl acetate) to afford the title compound as an off-white solid (470 mg, 94%). 1H NMR (DMSO-d6, 400 MHz): δ 1.485 (d, J=6.4 Hz, 6H), 2.601 (s, 3H), 3.945 (s, 3H), 5.121-5.186 (m, 1H), 7.523-7.554 (m, 1H), 7.902 (s, 1H), 8.232 (d, J=7.6 Hz, 1H), 8.316 (s, 1H), 8.625 (d, J=4 Hz, 1H), 9.045 (s, 1H).

Provenance & Evidence