Sodium Carbonate → 4-(2-Phenyl-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine

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Reaction Steps

A mixture of 191 mg (0.5 mmole) 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine, 60.9 mg (0.5 mmole) benzene-boronic acid, 55 mg sodium carbonate and 18 mg bis(triphenylphosphine)-palladium(II)-chloride is refluxed for 18 hours in 5 ml 1,2-dimethoxyethane and 0.25 ml water. The solvent is removed and the residue is diluted with dichloromethane. The dichloromethane solution is washed twice with water, dried over magnesiumsulfate and concentrated in vacuo. Flash chromatography (silicagel, ethyl acetate/hexane 1/1) of the residue yields 130 mg (68%) pure 4-(2-phenyl-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine as a pale yellow soild mp.: 255-258° C.

Provenance & Evidence