Potassium Carbonate → {5-[1-Biphenyl-4-ylmethyl-6-chloro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-phenyl}-phosphonic acid diethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of {5-[1-biphenyl-4-ylmethyl-6-chloro-5-Iodo-1H-benzoimidazol-2-yloxy]-2-methyl-phenyl}-phosphonic acid diethyl ester (900 mg, 1.3 mmol) in DMF (6 ml) was added 1-methyl-1H-indole-5-boronic acid (460 mg, 2.6 mmol), tetrakis(triphenylphosphine)-palladium(0) (155 mg, 0.13 mmol), and lastly a solution of potassium carbonate (718 mg, 5.2 mmol) in 3 ml of H2O. The mixture was heated in a microwave oven at 130° C. for 15 min. The reaction was partitioned between EtOAc and half-saturated NH4Cl. The EtOAc layer was washed with H2O and then brine. The organic layer was dried with MgSO4, evaporated to an oil, and then purified by flash chromatography. The flash column was eluted with a solvent gradient up to 65% EtOAc in Hexane to isolate the title compound as a mixture of the two protected regioisomers.

Provenance & Evidence