1-Fluoro-3-iodobenzene → 5-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester

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Reaction Steps

Add a 1 M solution of tetrabutylammonium fluoride (0.88 g, 3.38 mmol) in tetrahydrofuran to a mixture of 3-iodofluorobenzene (0.50 g, 2.25 mmol), 5-trimethylsilanylethynyl-nicotinic acid ethyl ester, (prepared as described in PREPARATION 16), (0.84 g, 3.38 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.03 g, 0.05 mmol) and copper (I) iodide (0.02 g, 0.09 mmol) at −78° C. Warm to room temperature, stir overnight and then dilute with ethyl acetate. Wash with an aqueous saturated solution of ammonium chloride, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 2.5:45:52.5 ethyl acetate:chloroform:hexanes, to give the title compound as a pale yellow solid (0.46 mg, 80%).

Provenance & Evidence