Potassium Carbonate → Methyl 1-(5-fluoropyridin-2-yl)-3-phenyl-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-phenyl-1H-pyrazole-4-carboxylate (0.50 g, 2.47 mmol) in toluene (9.9 mL) were added 2-bromo-5-fluoropyridine (0.52 g, 2.97 mmol), (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (78 μL, 0.50 mmol), copper(I) iodide (24.0 mg, 0.12 mmol) and potassium carbonate (0.72 g, 5.19 mmol). The mixture was heated in a microwave reactor for 20 min at 150° C. Additional (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (78 μL, 0.50 mmol) and copper(I) iodide (24.0 mg, 0.12 mmol) were added and the mixture was heated in the microwave reactor for another 20 min at 160° C. Saturated aqueous NaHCO3 was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts was dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (0.55 g). MS 298.1 (M+1).

Provenance & Evidence