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

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Reaction Conditions

Reaction Steps

diacetoxypalladium (6.15 mg, 0.03 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (150 mg, 0.55 mmol), 2-amino-4-fluoro-N- methylbenzamide (92 mg, 0.55 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (31.7 mg, 0.05 mmol) and cesium carbonate (268 mg, 0.82 mmol) in 1,4-dioxane (2.5 mL) under nitrogen. The resulting suspension was stirred at 100 °C for 16 hours. 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 (60.0 mg, 34.9 %) as a beige solid.

Provenance & Evidence