Sodium Carbonate → 4-[3-{6-[3-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-5-methanesulfonyl-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric Acid Ethyl Ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[3-[6-(3-bromo-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.0 g) in 1,2-dimethoxyethane (80 mL) were added 2,2-difluoro-benzo[1,3]dioxole-5-boronic acid (430 mg), 2 M aq. sodium carbonate solution (3.1 mL) and Pd(PPh3)4 (40 mg) and the resulting mixture was stirred at 85° C. for 3 h. Then the reaction mixture was diluted with ethyl acetate, filtered through Celite and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield the title compound (1.0 g, 89% yield). HRMS calcd for C37H44O10F2S [M+H]+ 719.2696, observed 719.2693.

Provenance & Evidence