Trimethylsilyl cyanide → 2-Fluoro-4-iodopyridine-5-acetonitrile

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Reaction Steps

Combine trimethylsilyl cyanide (297 mg, 3.0 mmol) and tetrabutylammonium fluoride (785 mg, 3.0 mmol) in 20 mL of acetonitrile under nitrogen. Add 5-bromomethyl-2-fluoro-4-iodo-pyridine (0.63 g, 2.0 mmol) to the above solution. Stir the mixture for 2 h at RT. Dilute the mixture with chloroform/IPA (3/1). Wash the solution with water and subsequently with saturated aqueous sodium chloride. Dry it over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (5% methanol in DCM) to afford the title compound as a yellow, waxy solid (500 mg, 96%). MS (ES) m/z 263 [M+1]+.

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