Tetrahydrofuran → N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

A dry 25 mL flask was charged with 2,5-dimethyl-2H-pyrazole-3-carbonyl chloride (0.135 g, 0.854 mmol) and THF (5 mL) was added. 3-Ethynyl-phenylamine (0.100 g, 0.854 mmol) was added to the THF solution of the acid chloride followed by NEt3, and the mixture was allowed to stir at 55° C. The reaction mixture was then allowed to cool to room temperature. The reaction was extracted twice with EtOAc (˜5 mL) and water (˜10 mL) followed by saturated aqueous NaHCO3(˜10 mL). The combined organic layers were dried over anhydrous Na2SO4 (s) and then concentrated. The crude residue was purified by chromatography (silica gel, gradient elution EtOAc/Hexanes 0 to 60%). The product containing fractions were concentrated to give the title compound as a tan solid (147 mg. 72%).

Provenance & Evidence