Ethylenediamine → HCID 66616721, compound

Participants

Reaction Steps

To a solution of methyl 4-(1H-pyrrol-3-yl)-benzoate in anhydrous dioxane (67 mL) is added 4-iodobenzotrifluoride (4.39 g, 16.1 mmol), cuprous iodide (0.255 g, 1.34 mmol), ethylenediamine (81 mg, 1.35 mmol) and potassium phosphate (10.16 g, 44.1 mmol). The reaction mixture is heated at reflux for 20 h. under a nitrogen atmosphere, then cooled to room temperature. The solid is filtered, washed with ethyl acetate and discarded. The filtrate is concentrated to give a dark solid which is diluted with water (50 mL) and extracted with ethyl acetate (3×20 mL). The extracts are washed with water (2×20 mL), combined, dried over MgSO4 and concentrated to give the crude product. The crude product is purified by silica gel chromatography (5-20% ethyl acetate) to give 2.00 g of methyl 3-[1-(4-trifluoromethyl-phenyl)-1H-pyrrol-3-yl]-benzoate as a white solid (73% yield). 1H NMR (300 MHz, DMSO-d6): δ 3.93 (s, 3H), 6.75 (m, 1H), 7.19 (in, 1H), 7.50 (m, 1H), 7.55 (d, 2H, J=8.7 Hz), 7.63 (d, 2H, J=6.6 Hz), 7.73 (d, 2H, J=8.4 Hz), 8.04 (d, 2H, J=6.6 Hz).

Provenance & Evidence