5-Ethynyl-1-methyl-1H-imidazole → Acetic acid 2,6-dimethoxy-3-(3-methyl-3H-imidazol-4-ylethynyl)-phenyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-acetoxy-2,4-dimethoxy-iodobenzene (250 mg, 0.776 mmol) and 5-ethynyl-1-methyl-1H-imidazole (100 mg, 1.09 mmol) in dry MeCN (3 ml) and dry NEt3 (1 ml) was added Pd(Ph3P)2Cl2 (20 mg, 3.7 mol %) and the reaction vessel was evacuated and backfilled with N2(g) three times. Copper (I) iodide (15 mg) was added and the reaction was heated to 60° C. and stirred overnight. The resulting dark solution was cooled, diluted with EtOAc and filtered through celite. The filtrate was concentrated onto silica-gel under reduced pressure and the solid residue was purified by flash chromatography (silica-gel, eluted with EtOAc) to give the product as a tan solid (130 mg, 56%). 1H-NMR (300 MHz, CDCl3) δ 7.45 (br s, 1H), 7.30 (d, J=8.7 Hz, 1H), 7.30 (br s, 1H), 6.68 (d, J=8.7 Hz, 1H), 3.94 (s, 3H), 3.83 (s, 3H), 3.71 (s, 3H), 2.33 (s, 3H).

Provenance & Evidence