Dimethylacetamide → (S)-2-sec-Butylamino-6-cyano-isonicotinic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Dissolve (S)-2-sec-butylamino-6-chloro-isonicotinic acid methyl ester (800 mg, 0.34 mmol), tris(dibenzylideneacetone)dipalladium (0) (120 mg, 0.13 mmol), 1,1′-bis(diphenylphosphino)ferrocene (146 mg, 0.26 mmol), zinc dust (52 mg) and zinc (II) cyanide (387 mg, 3.3 mmol) in N,N-dimethylacetamide (6.6 mL) ) in a previously nitrogen-filled sealed vessel. Flush the reactants with nitrogen before sealing and heat for 6 h at 130° C. Cool to room temperature, dilute with ethyl acetate and wash with 2 N ammonium hydroxide. Wash the organic layer with saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 0:100 to 05:95 ethyl acetate:hexanes) to give the title compound.

Provenance & Evidence