Chemo- and regioselective ethynylation of 4,5,6,7-tetrahydroindoles with ethyl 3-halo-2-propynoates

4,5,6,7-Tetrahydroindoles undergo a rapid, facile (rt, 60 min) ethynylation with ethyl 3-halo-2-propynoates upon grinding with solid K2CO3 (without solvent) at C-2 of the tetrahydroindole ring to afford ethyl 3-(4,5,6,7-tetrahydroindol-2-yl)-2-propynoates in 62-90% yield.