Triethylamine → 3-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-2-methyl-acrylic acid ethyl ester

Participants

Reaction Steps

Following General Procedure B and using cyclopropyl-(3-ethynyl-benzyl)-methyl-amine (Intermediate 91, 0.1 g, 0.54 mmol), (E)-3-(4-iodo-phenyl)-2-methyl-acrylic acid ethyl ester (Reagent 7, 0.17 g, 0.54 mmol), triethyl amine (10 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.071 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 2-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.15 g, 75%). 1H NMR (300 MHz, CDCl3): δ 7.66-7.25 (m, 9H), 4.27(q, J=7.3 Hz, 2H), 3.65(s, 2H), 2.25(s, 3H), 2.13 (d, J=1.2 Hz, 3H), 1.75-1.65(m, 1H), 1.35(t, J=7.3 Hz, 3H), 0.50-0.40(m, 4H).

Provenance & Evidence