Sodium Iodide → [Rac]-[4-(methyl-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethyl}-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester

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Reaction Conditions

Reaction Steps

0.095 g (0.37 mmol) of the above prepared (4-methylamino-naphthalen-1-yloxy)-acetic acid ethyl ester and 0.220 g of [rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (see below 1G], 2.0 eq.) were treated in 2.8 ml of DMSO with 0.110 g (1 eq.) of NaI and 0.168 g (1.5 eq.) of DBU. After stirring for 20 h at 40° C., the reaction mixture was poured onto crashed ice/KHSO4, extracted twice with AcOEt, washed with water and brine, and dried over sodium sulfate. Evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=85/15), afforded 0.055 g of the title compound as light brown oil.

Provenance & Evidence