Triethylamine → 2-Methyl-2-{2-methyl-4-[5-(5-trifluoromethyl-pyridin-2-yl)-pent-4-ynyloxy]-phenoxy}-propionic acid ethyl ester

Participants

Reaction Steps

A degassed (argon) solution of 152 mg (0.50 mmol) 2-methyl-2-(2-methyl-4-pent-4-ynyloxy-phenoxy)-propionic acid ethyl ester (example 13A]), 124 mg (0.55 mmol) 2-bromo-5-(trifluoromethyl)pyridine and 0.21 ml (1.5 mmol) Et3N in 5 ml acetonitrile was treated with 18 mg (0.03 mmol) of PdCl2(PPh3)2 and 3 mg (0.03 mmol) of CuI. After stirring for 3 h at room temperature the reaction mixture was partitioned between cold aqueous 10% KHSO4 and ether (three times). Washing of the organic layer with aqueous 10% NaCl solution, drying (Na2SO4) and evaporation of the solvents, followed by flash chromatography (SiO2, n-heptane/EtOAc 95:5 to 9:1) yielded 170 mg of the title compound as yellow viscous oil.

Provenance & Evidence