Sodium Carbonate → HCID 13546598, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 1 g (5.76 mmol) of 2-amino-6-chloro-3-nitropyridine is mixed with 1.26 g (8.07 mmol) of 4-chlorobenzeneboronic acid, 7.2 ml (14.4 mmol) of a 2M aqueous solution of sodium carbonate and 0.7 g (16.36 mmol) of lithium chloride in 44 ml of a pre-degassed mixture of ethanol/toluene/water (v/v: 1/1/0.4). 0.34 g (0.29 mmol) of tetrakis(triphenylphosphine)palladium(0) is added. The mixture is heated at 90° C. with stirring for 18 hours. The resulting mixture is cooled to ambient temperature and then diluted with 50 ml of dichloromethane and 25 ml of water. The organic phase is separated by settling out and washed with 25 ml of water and 25 ml of a saturated solution of sodium chloride. The resulting product is dried over sodium sulfate and evaporated to dryness. The product is purified by silica gel chromatography, elution being carried out with a 50:50 then 80:20 mixture of dichloromethane and cyclohexane. 0.395 g (yield: 27%) of 6-(4-chlorophenyl)-3-nitropyridin-2-ylamine is obtained in the form of a white powder.

Provenance & Evidence