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

関与物質

反応条件

反応手順

palladium acetate (31.2 mg, 0.14 mmol) was added to 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (121 mg, 0.21 mmol), Cesium carbonate (2266 mg, 6.95 mmol), 2-amino-5-fluoro-N-methylbenzamide (585 mg, 3.48 mmol) and 2,5-dichloro-4-iodopyridine (1000 mg, 3.65 mmol) in dioxane (20 mL) under nitrogen. The resulting suspension was stirred at 80 °C for 18hrs then cooled. Product appeared to be out of solution. Product and bis product suggested. Disappointing! The reaction mixture was evaporated to dryness and redissolved in EtOAc (100 mL), and washed sequentially with saturated Na2CO3 (50 mL), water (50 mL), and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford desired product as an beige solid.

情報源と証拠