In a clean, oven dried round bottom flask with stir bar, 1 (342 mg, 0.78 mmol) and copper iodide (0.2 eq., 0.158 mmol) were dissolved in 5 ml dry DMF. The flask was evacuated under high vacuum and refilled with argon several times. Under argon, the flask was capped with a septum and argon was allowed to bubble through a needle through the solution for 20 min. 0.1 equivalents (55 mg, 0.16 mmol) of Bis(triphenylphosphine)palladium(II) Dichloride was added to the solution while still under argon. To the capped solution, trimethylsilylacetylene (1.5, eq., 164 µl, 1.18 mmol) of was added via syringe. To this solution, triethylamine was added (three eq., 330 µl, 2.37 mmol) via syringe. The reaction was covered in aluminum foil and a balloon filled with argon was placed into the septum of the capped reaction and the reaction was allowed to progress, stirring overnight at RT. The reaction turned a deep brown color overnight. DMF was evaporated in vacuo in a water bath set to 40 °C. The residue was taken up into 25 ml ethyl acetate and remaining DMF was extracted from the organic layer with 25 ml brine (3X). The organic layer was dried over sodium sulfate, concentrated and purified via combi flash (MP A: hexanes, MP B: ethyl acetate; 0–3 min: 0–100%B, 3–18 min: 100%B). Fractions containing desired compound were pooled and concentrated to yield 191 mg of product 60% yield. 1H NMR (400 MHz, DMSO-d6) δ 8.44 (s, 1H), 7.55 (s, 2H), 6.08 (d, J = 2.9 Hz, 1H), 5.28 (dd, J = 6.1, 2.9 Hz, 1H), 5.20–5.08 (m, 1H), 4.95 (dd, J = 6.1, 2.7 Hz, 1H), 4.22 (s, 1H), 3.54 (t, J = 5.1 Hz, 2H), 1.56 (s, 3H), 1.34 (s, 3H), 0.25 (d, J = 1.0 Hz, 9H).