Methyl iodide → HCID 10108758, compound

Participants

Reaction Steps

Preparation of compound 12(b)(i) and compound 12(b)(ii) (2-(4-fluoro-phenyl)-5-methoxy-benzofuran-3-carboxylic acid methyl ester and 2-(4-fluoro-phenyl)-5-methoxy-benzofuran-3-carboxylic acid ethyl ester). Methyl iodide (0.43 mL, 6.99 mmol) was added to a mixture of the compounds 12(a)(i) and 12(a)(ii) (1.00 g, 3.49 mmol), potassium carbonate (milled, 1.21 g, 8.73 mmol) and anhydrous acetonitrile (15 mL) under an argon atmosphere. The reaction mixture was heated to reflux under argon for 18 hours, and then cooled to room temperature and stirred for 24 hours. The mixture was diluted with acetonitrile (10 mL) and filtered, followed by evaporation of the solvent. The crude solid was diluted with 60:40 ethyl acetate/hexanes, refiltered, and purified by HPLC (silica gel, ethyl acetate/hexanes) to provide 0.85 g (78%) of the desired product.

Provenance & Evidence