2,5-Dichloro-4-iodopyridine → 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

2,5-dichloro-4-iodopyridine (250 mg, 0.91 mmol), 2-amino-4-fluoro-N- methylbenzamide (169 mg, 1.00 mmol) diacetoxypalladium (10.25 mg, 0.05 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (52.8 mg, 0.09 mmol) and cesium carbonate (446 mg, 1.37 mmol) were dissolved in 1,4-dioxane (2.5 mL) and sealed into a microwave tube. The reaction was degased, purged with nitrogen and heated to 140 °C over a period of 30 minutes in the microwave reactor. The mixture was cooled to RT; filtered the solvent was evaporated. The crude product was absorbed on silica gel and purified by flash chromatography on silica gel eluting with 20 to 80% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide (175 mg, 61.0 %) as a beige solid.

Provenance & Evidence