Potassium Phosphate, Tribasic → {5-[4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-pyridin-3-yl}-acetic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

Degassed N,N-dimethylformamide (0.12 mL) was added to t-butyl-(1-{2-[4-(1-ethyl-1-{4-[4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)dimethylsilane (Example 23-(1); 11.0 mg, 0.0181 mmol), (5-bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 6.3 mg, 0.027 mmol), tetrakis(triphenylphosphine)palladium (0) (2.6 mg, 0.0022 mmol) and potassium phosphate (9.0 mg, 0.042 mmol). After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 81 to 92° C. for three hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/dichloromethane=3/1) to give the title compound (9.5 mg, 83%).

Provenance & Evidence