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

Participants

Reaction Steps

To 0.164 g (0.523 mmol) of [rac]-3-(1-chloro-propyl)-2-methyl-6-(3-trifluoromethyl-phenyl)-pyridine (see below 2C]) and 0.149 g (0.575 mmol) of the above prepared (4-methylamino-naphthalen-1-yloxy)-acetic acid ethyl ester, dissolved in 3.2 ml of abs. DMSO, were added successively 0.0867 g of K2CO3 (0.627 mmol) and 0.0856 g (0.575 mmol) of NaI. The reaction was allowed to proceed for 15 h at 60° C. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9/1), yielded 0.043 g of the title compound as light yellow oil.

Provenance & Evidence