A solution of 2 (2.00 g, 3.82 mmol), phenylacetylene (0.47 mL, 4.28 mmol), Pd(PPh3)2Cl2 (137 mg, 0.19 mmol), K2CO3 (542 mg, 3.92 mmol), and Et3N (0.55 mL, 3.95 mmol) in DMF (5 mL) was stirred for 24 h at room temperature. Water (10 mL) was added to the mixture and then extracted with Et2O (3×30 mL). The combined organic layer was washed with brine (3×15 mL), dried over MgSO4, and then concentrated in vacuo. MPLC purification (Hex:EtOAc/5:1) of the residue gave 3 as a yellow amorphous solid (1.37 g, 72%). 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 8.04 (d, J=8.0 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H), 7.63-7.61 (m, 2H), 7.52 (s, 1H), 7.43-7.37 (m, 3H), 4.19 (q, J=7.2 Hz, 2H), 3.67 (s, 2H), and 1.28 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 183.93, 169.64, 149.51, 142.13, 136.97, 136.36, 135.90, 135.24, 132.92, 132.52, 130.11, 128.82, 125.57, 124.25, 122.73, 122.06, 101.10, 84.72, 61.75, 35.26, and 14.42.
