Thionyl Chloride → N-(2-bromo-6-methoxy-3-pyridinyl)-2-methylnicotinamide

Participants

Reaction Steps

To a suspension of potassium 2-methylnicotinate (1.96 g) in chloroform (30 mL) was added thionyl chloride (2.5 mL). The mixture was stirred overnight at room temperature under a drying tube. Diisopropylethylamine (5 mL) was added followed by 3-amino-2-bromo-6-methoxypyridine (2.25 g). After 10 minutes additional diisopropylethylamine (5 mL) was added. After 2 hours the mixture was diluted with chloroform, washed with water, dried (Na2SO4,) filtered, and evaporated. Chromatography of the residue over silica gel (chloroform/methanol) gave N-(2-bromo-6-methoxy-3-pyridinyl)-2-methylnicotinamide (2.80 g).

Provenance & Evidence