(Diethylamino)sulfur trifluoride → HCID 22677439, compound

Participants

Reaction Steps

(Diethylamino)sulfur trifluoride (0.73 mL, 5.5 mmol) was added dropwise to a solution of methyl 4-amino-3-chloro-6-(4-hydroxymethylphenyl)pyridine-2-carboxylate (1.46 g, 5.0 mmol) in dichloromethane (35 mL) at 0° C. The reaction mixture was stirred for 15 minutes and then quenched with ice followed by water. The product was extracted with ethyl acetate and the organic phase was washed with brine and concentrated. The residue was purified by column chromatography (dichloromethane/hexane) giving methyl 4-amino-3-chloro-6-(4-fluoromethylphenyl)pyridine-2-carboxylate (480 mg, 1.6 mmol), mp 95-97° C.

Provenance & Evidence