Sodium Carbonate → HCID 57586506, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-{3-[6-(3,5-dibromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (321 mg, 0.5 mmol) in dimethoxyethane (10 mL) was stirred for 5 minutes at room temperature under a nitrogen atmosphere. Then, tetrakis(triphenylphosphine)palladium(0) (115 mg, 0.1 mmol) was added at room temperature and the resulting light yellow solution was heated to 80° C. and stirred for 5 minutes. At this point, a solution of pyridin-4-ylboronic acid (368 mg, 3.0 mmol) in ethanol (10 mL) was added followed by a solution of sodium carbonate (318 mg, 3.0 mmol) in water (1.0 mL). The resulting light yellow suspension was stirred for 24 h at reflux. Then, the reaction mixture was cooled to room temperature and diluted with water (20 mL) and ethyl acetate (50 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic extracts were washed with water (100 mL), brine solution (100 mL), and dried over anhydrous magnesium sulfate. Filtration and concentration of the solvent gave the crude residue which was purified by using an ISCO 40 g column, eluting with 0-50% ethyl acetate/hexanes to afford 4-{3-[6-(3,5-di-pyridin-4-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (205 mg, 64%) as a light brown oil: ES(+)-HRMS m/e calculated for C39H46N2O6 (M+H)+ 639.3429, found 639.3426.

Provenance & Evidence