Ammonium Chloride → [5-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-2-yl]-acetic Acid Methyl Ester

Participants

Reaction Steps

A solution of 2-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 32-(4); 60.8 mg, 0.10 mmol), (5-bromo-pyridin-2-yl)acetic acid methyl ester (Example 44-(2); 43.5 mg, 0.18 mmol), tetrakistriphenylphosphine palladium (17.3 mg, 0.015 mmol) and potassium phosphate (34.1 mg, 0.16 mmol) in N,N-dimethylformamide (0.6 mL) was stirred at 85° C. for four hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (20% ethyl acetate/hexane to 60% ethyl acetate/hexane) to give the title compound (18.1 mg, 28%).

Provenance & Evidence