Cesium carbonate → 3-[1-ethyl-5-(4-isopropylphenoxy)-1H-pyrazol-3-yl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

Dioxane (4.7 mL) was added to a mixture of 3-(1-ethyl-5-oxo-2,5-dihydro-1H-pyrazol-3-yl)benzonitrile (500 mg, 2.35 mmol, 1 equiv), cesium carbonate (1.53 g, 4.69 mmol, 2.00 equiv), copper (I) iodide (112 mg, 0.586 mmol, 0.250 equiv) and N,N-dimethylglycine hydrochloride (164 mg, 1.17 mmol, 0.50 equiv). The reaction flask was sealed, and nitrogen gas was bubbled through the reaction mixture for 5 minutes with a needle. The needle was removed, and 1-bromo-4-isopropylbenzene (934 mg, 4.69 mmol, 2.00 equiv) was added. The reaction flask was sealed and heated to 110° C. for 16 hours. The crude reaction mixture was loaded directly onto a silica gel column and purified by flash-column chromatography (hexanes, grading to 50% ethyl acetate-hexanes) to afford 3-[1-ethyl-5-(4-isopropylphenoxy)-1H-pyrazol-3-yl]benzonitrile (165 mg, 21%). Calcd (M+1)+: 332.2. Found: 332.1.

Provenance & Evidence