Ethylenediamine → HCID 66616140, compound

Participants

Reaction Steps

To a stirred solution of methyl 4-(1H-pyrrol-3-yl)-benzoate (402 mg, 1.997 mmol, 1.0 eq.) and 4-trifluoromethyl-1-iodobenzene (652 mg, 2.39 mmol, 1.2 eq.) in anhydrous 1,4-dioxane (15 mL) is added copper(I) iodide (38 mg, 0.199 mmol, 0.1 eq.), ethylenediamine (13 μL, 0.199 mmol, 0.1 eq.) and potassium triphosphate (762 mg, 1.66 mmol, 3.31 eq.). The reaction mixture is degassed, flushed with nitrogen and heated to reflux for 18 hr. The reaction mixture is cooled, filtered and washed with ethyl acetate. The filtrate is concentrated and purified by silica gel chromatography (10% ethyl acetate/hexane) to get a white powder, methyl 4-[1-(4-trifluoromethyl-phenyl)-1H-pyrrol-3-yl]-benzoate (363.2 mg, 1.05 mmol, 52.7%). MS (ES+): m/e 345.11. 1H NMR (300 MHz, CDC3): δ 8.04 (2H, d, J=8 Hz), 7.72 (2H, d, J=8 Hz), 7.63 (2H, d, J=8 Hz), 7.54 (2H, d, J=8 Hz), 7.50 (1H, m), 7.18 (1H, m), 6.75 (1H, m), 3.93 (3H, s).

Provenance & Evidence