4-Fluoroiodobenzene → HCID 57963782, compound

Participants

Reaction Steps

To a solution of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (100 mg, 0.480 mmol) in toluene (0.5 mL) was added (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (13.67 mg, 0.096 mmol), 1-fluoro-4-iodobenzene (0.166 mL, 1.441 mmol), potassium carbonate (139 mg, 1.009 mmol), and copper(I) iodide (9.00 mg, 0.047 mmol). This reaction was heated to reflux overnight. The next day, the reaction was complete by HPLC so it was filtered through a frit with EtOAc and purified on a SiO2 column using 25-100% EtOAc hexanes gradient to give white crystalline ethyl 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (140 mg, 0.463 mmol, 96% yield). The structure was assigned by small molecule X-ray crystallography. 1H NMR (400 MHz, CDCl3) δ ppm 8.35 (1H, s), 7.62 (2H, m), 7.14 (2H, m), 4.25 (2H, q), 1.37 (3H, t).

Provenance & Evidence