5-Chloro-2-fluoro-4-iodopyridine → 4-(((5-chloro-4-iodopyridin-2-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile

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Reaction Steps

A solution of 5-chloro-2-fluoro-4-iodopyridine (1 g, 3.88 mmol) and 4-(aminomethyl)tetrahydro-2H-pyran-4-carbonitrile (1.634 g, 11.65 mmol) in 4 mL of dimethylsulfoxide was heated at 100° C. for 8 hours. The mixture was quenched with 100 mL of ice-cold water and was extracted with ethyl acetate (50 mL×2). The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 20% ethyl acetate in hexane) afforded the title compound.

Provenance & Evidence