Potassium Carbonate → {4'-Bromo-2'-[(tert-butoxycarbonyl-ethyl-amino)-methyl]-6-methoxy-biphenyl-3-yl}-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

(5-Bromo-2-iodo-benzyl)-ethyl-carbamic acid tert-butyl ester (2.0 g, 4.54 mmol), [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (1.67 g, 5.21 mmol), and potassium carbonate (1.57 g, 11.4 mmol) were combined in DME:H2O (2:1) under nitrogen. The mixture was purged with nitrogen, and then tetrakis(triphenylphosphine)palladium(0) (0.150 g, 0.13 mmol) was added, and the reaction was heated to 80° C. for 36 hours. Once no starting material was seen by analytical LCMS, the mixture was cooled to room temperature and diluted with dichloromethane and water. The aqueous layer was separated and extracted with dichloromethane, and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-100% ethyl acetate in hexanes) to give the title compound.

Provenance & Evidence