Triethylamine → HCID 22677634, compound

Participants

Reaction Steps

To a solution of ethyl 2-(N-methylprop-2-ynoylamino)acetate (312 mg, 1.84 mmol) in THF (6 mL) was added 3-iodoanisole (475 mg, 0.24 mL, 2.03 mmol), dichlorobis(triphenylphosphine)palladium(II) (133 mg, 0.19 mmol), copper(I) iodide (36 mg, 0.19 mmol) and Et3N (279 mg, 0.39 mL, 2.76 mmol). The resulting mixture was stirred in dark for 2 h. A saturated NH4Cl solution (30 mL) was then added and the mixture was extracted with EtOAc (2×30 mL). The combined organic layers were washed with a saturated NaCl solution (60 mL), dried (Na2SO4) and concentrated under reduced pressure to give a dark oil, which was dissolved in EtOAc and filtered through a pad of silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography (33% EtOAc/hex) to give ethyl 2-[3-(3-methoxyphenyl)-N-methylprop-2-ynoylamino]acetate (175 mg, 35%) as a light yellow oil: 1H NMR (CDCl3; a mixture of two rotomers) δ 1.30 (t, J=7.0 Hz, 3H), 3.10 (1.35H), 3.36 (s, 1.65H), 3.81 (s, 1.35H), 3.82 (s, 1.65H), 4.20-4.30 (m, 3.2H), 4.39 (s, 0.8H), 6.97-7.29 (m, 4H); HPLC ES-MS m/z (rel abundance) 276 (MH+, 100%).

Provenance & Evidence