Water → {5-[1-Benzyl-6-chloro-5-(4-cyclohexyl-phenyl)-1H-benzoimidazol-2-yloxy]-2-methyl-phenyl}-phosphonic acid diethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of [5-(1-Benzyl-6-chloro-5-iodo-1H-benzoimidazol-2-yloxy)-2-methyl-phenyl]-phosphonic acid diethyl ester (5.2 g, 8.5 mmol) in toluene (30 ml) was added 4-cyclohexylbenzeneboronic acid (3.5 g, 17 mmol), tetrakis(triphenylphosphine)palladium(0) (983 mg, 0.9 mmol), and then potassium carbonate (4.7 g, 34 mmol) in a solution of H2O (15 ml). The resulting mixture was heated in a microwave reactor at 130° C. for 15 minutes, and then quenched with saturated ammonium chloride solution. The mixture was then partitioned between EtOAc and H2O. The organic layer was washed with H2O, brine, and then dried with MgSO4. The crude mixture was then purified by flash chromatography (SiO2, 80 g). The title compound was eluted with 60% EtOAc in Hexane.

Provenance & Evidence