Potassium Carbonate → HCID 67976104, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 1,4-dioxane/H2O (30 mL/5 mL). The flask was cooled to 0° C. and vacuum was applied for 20 minutes. A second flask was charged with 3-bromo-1-((1-isopropyl-5-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole (1.95 g, 5.16 mmol), K2CO3 (2.85 g, 20.6 mmol), diacetoxypalladium (0.0579 g, 0.258 mmol), methylboronic acid (0.926 g, 15.5 mmol) and sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate (0.264 g, 0.516 mmol). The second flask was evacuated with and back filled with nitrogen three times. The cold degassed dioxane/H2O was added to the second flask, which was evacuated and back filled with argon 5 times. The reaction mixture was heated to 80° C. for 3 hours. The reaction was cooled to ambient temperature and filtered, and concentrated under reduced pressure. The residue was diluted with EtOAc (200 mL). The organic layer was washed with saturated NaHCO3 (30 mL), dried (Na2SO4) and concentrated to give 1.34 g (83%) of the title compound, which was used in the next step without further purification.

Provenance & Evidence