Cesium carbonate → 2-(2-Chloro-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

2-Chloro-4-iodo-5-(trifluoromethyl)pyridine (420 mg, 1.37 mmol), 2-amino-6-methoxy-N-methylbenzamide (246 mg, 1.37 mmol), palladium(II) acetate (24.54 mg, 0.11 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (126 mg, 0.22 mmol) and cesium carbonate (534 mg, 1.64 mmol) were mixed together in dioxane (8 mL). Reaction was degassed with argon and was stirred at 90° C. overnight (15 hours) under argon. The reaction mixture was filtered, washed with DCM and the filtrate was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 10 to 30% EtOAc in petroleum ether. The solvent was evaporated to dryness to afford 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy-N-methylbenzamide (325 mg, 66%) as a white solid. 1H NMR spectrum (500 MHz, DMSO): 2.68 (d, 3H), 3.83 (s, 3H), 6.84 (s, 1H), 7.03 (d, 1H), 7.08 (d, 1H), 7.47 (dd, 1H), 8.19 (q, 1H), 8.42 (s, 1H), 9.15 (s, 1H); Mass spectrum: ESI+ MH+ 360.

Provenance & Evidence