Sodium hydride → N,N-dimethyl-2-((4-methylpyridin-3-yl)amino)benzamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-amino-N,N-dimethylbenzamide (1.3 g, 6.77 mmol), 3-chloro-4-methylpyridine (0.745 mL, 6.77 mmol), Palladium acetate (0.150 g) and BINAP (0.60 g) in 1,4-dioxane (10 mL) was added NaH (0.677 g, 16.93 mmol) and the resulting mixture was heated at 100° C. for 2 hours. The solvent was removed under reduced pressure. The residue obtained was taken into dichloromethane (50 mL) and filtered through celite. The filtrate was washed with water (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified using flash column chromatography (SiO2) to provide 0.450 g of the desired product as a dark oil.

Provenance & Evidence