Sodium hydride → 6-chloro-N-(5-methyl-4-phenyl-1,3-thiazol-2-yl)pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-methyl-4-phenyl-thiazol-2-ylamine (2.0 g, 10.5 mmol) in anhydrous tetrahydrofuran (40 mL) and methylene chloride (40 mL) in a round bottom flask under argon was carefully added sodium hydride (60% in mineral oil, 1.7 g, 42.5 mmol). The mixture was heated in a 60° C. oil bath for one hour, then chilled in an ice bath and 6-chloro-nicotinoyl chloride (2.03 g, 11.6 mmol) was added followed by diisopropylethylamine (7.32 mL, 42.1 mmol). The mixture was heated under argon in an oil bath at 60° C. for two hours and stirred at room temperature overnight. After dilution with methanol, the mixture was loaded onto silica gel and chromatographed using a mixture of ethyl acetate/hexanes to give 6-chloro-N-(5-methyl-4-phenyl-thiazol-2-yl)-nicotinamide (1.0 g, Yield: 29%).

Provenance & Evidence