Potassium Carbonate → 3-((3-Cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one

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To a 50 mL pear shaped flask was added 4-dioxane/water (3.2 mL/0.6 mL). The flask was cooled in an ice/water bath before applying vacuum for 20 minutes. 3-((3-Bromo-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one (0.55 g, 1.52 mmol), cyclopropylboronic acid (0.33 g, 3.79 mmol), sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate (0.047 g, 0.091 mmol), palladium acetate (0.01 g, 0.4 mmol), and potassium carbonate (0.84 g, 6.07 mmol) were combined in a 25 mL round bottom flask and placed under vacuum. The degassed solvent mixture was added to the solid reagents and the flask was affixed with a condenser. The apparatus was evacuated and back filled with argon 5 times before heating at reflux under argon for 5 hours. The mixture was cooled to ambient temperature and filtered through a pad of Celite®. The filter cake was washed with ethyl acetate and water. The filtrate phases were separated and the aqueous phase was extracted with ethyl acetate 3 times. The combined organic extracts were washed with saturated sodium bicarbonate 3 times. The organic phase was concentrated under vacuum and dried under high vacuum to give 3-((-cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridine-2(1H)-one as a beige solid (413 mg).

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