Sodium Carbonate → Ethyl 5-(2-chloro-5-(6-(difluoromethoxy)pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of ethyl 5-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate (Preparation 5, 229 mg, 0.44 mmol) in dioxane (4 mL) and water (0.5 mL) heated to 50° C. was added Na2CO3 (228 mg, 1.32 mmol), Cataxium A (16 mg, 0.044 mmol), a solution of 2-bromo-6-(difluoromethoxy)pyridine (Preparation 58, 100 mg, 0.44 mmol) in dioxane (1 mL) and Pd(OAc)2 (5 mg, 0.022 mmol). The reaction was heated at 80° C. for 3 hours. Further Cataxium A (16 mg, 0.044 mmol) and Pd(OAc)2 (5 mg, 0.022 mmol) were added and the reaction continued at 90° C. for 3 hours. The reaction was cooled and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 10-40% EtOAc in heptanes to afford the title compound (146 mg, 60%).

Provenance & Evidence