Tetramethyltin → 5,6-Dimethoxy-3-methyl-2-pyridinecarbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-chloro-5,6-dimethoxypyridine-2-carbonitrile (1-6d, 1 g, 5.04 mmol) in DMF (20 mL) was added lithium chloride (2.1 g, 50.4 mmol), Pd(PPh3)4 (1.16 g, 1.0 mmol) and tetramethyltin (4.5 g, 25.2 mmol). The resulting mixture was heated at 100° C. overnight, cooled to rt, diluted with saturated ammonium chloride and extracted with EtOAc. The combined organic layers were dried and concentrated to give a yellow oil which was purified by column chromatography (SiO2, 80 g, 0-30% EtOAc in hexane) to give 1-6e as a bone powder. ESI+ MS [M+H]+ C9H11N2O2=179.1.

Provenance & Evidence