Cesium carbonate → HCID 68688049, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 520 mg of 2-chloro-3-methylisonicotinic acid methyl ester [48-1], 161 mg of bis(dibenzylideneacetone)palladium, 324 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 1.28 g of cesium carbonate, 564 μL of benzophenoneimine, 5 mL of 1,4-dioxane, and 5 mL of toluene, was stirred overnight at 80° C. After cooling the reaction mixture back to room temperature, water and a saturated aqueous solution of sodium bicarbonate were added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the obtained residue was dissolved in 28 mL of methanol. Thereto, 1.1 g of sodium acetate and 700 mg of hydroxyamine hydrochloride were added, and stirred for 1 hour. Then, a 0.1 N aqueous solution of sodium hydroxide was added, and extracted with chloroform. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, to obtain 92.1 mg of 2-amino-3-methylisonicotinic acid methyl ester [48-2] as a yellow solid.

Provenance & Evidence