2-Amino-N-methylbenzamide → 2-[2-Chloro-5-(trifluoromethyl)pyridin-4-ylamino]-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

2-chloro-4-iodo-5-(trifluoromethyl)pyridine (7 g, 22.77 mmol), 2-amino-N- methylbenzamide (3.42 g, 22.77 mmol), diacetoxypalladium (0.409 g, 1.82 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.108 g, 3.64 mmol) and cesium carbonate (8.90 g, 27.32 mmol) were mixed together in dioxane (140 mL). Reaction was degassed with nitrogen and was stirred at 90 °C overnight under nitrogen. Reaction was filtered, washed with CH2Cl2 and filtrate was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 10 to 50% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (5.06 g, 67.4 %) as a pale yellow solid.

Provenance & Evidence