Toluene → HCID 10224467, compound

Participants

Reaction Steps

To a mixture of 0.1 g (0.23 mmol) of 2-bromo-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-pyridine-3-carbonitrile (Example 3), 10 ml of toluene and 4 ml of ethanol was added 34 mg (0.28 mMol) of phenylboric acid and a solution of 71 mg (0.52 mMol) of K2CO3 in 1 ml water. To the resulting reaction mixture was added 18 mg of tetrakis(triphenylphosphine)palladium. The mixture was held at reflux overnight, cooled to room temperature, poured into 75 ml of water and extracted with dichloromethane. The combined organic solutions were washed once with 10% NaOH solution, once with brine, dried over MgSO4 and evaporated to dryness to give a yellowish oil which crystallized upon standing. Trituration with ether gave 74.5 mg (76%) of a white powder: m.p. 230-231° C.

Provenance & Evidence