Compound 3'

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Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Compound 2’ (1.29 g, 3.00 mmol), CuI (57.1 mg, 0.30 mmol) and Pd(PPh₃)₄ (173 mg, 0.15 mmol) were added into a two necked flask, degassed and filled back with Argon three times, then dry toluene (90 mL), diisopropylamine (36 mL) and trimethylsilylacetylene (0.43 mL, 3.02 mmol) were added through syringe respectively. The reaction mixture was stirred at room temperature for 1 day, then all the solvents were removed under vacuum, the remaining solid was extracted by dichloromethane (120 mL), washed with water, brine, dried over Na₂SO₄, filtered and concentrated. The crude was purified by flash chromatography (Hexane) to give compound 3’ as white solid (592 mg, 49%). Data for 3’: ¹H NMR (500 MHz, CDCl₃): δ 0.30 (s, 9H), 7.60 (d, J = 9.0 Hz, 1H), 7.67 (d, J = 9.0 Hz, 1H), 7.70 (d, J = 8.5 Hz, 1H), 7.89 (d, J = 8.5 Hz, 1H), 8.01 (s, 1H), 8.24 (s, 1H), 8.33 (d, J = 8.5 Hz, 1H), 8.52 (d, J = 8.5 Hz, 1H). ¹³C NMR (125 MHz, CDCl₃): δ 0.14, 92.8, 95.6, 105.1, 121.9, 122.6, 124.7, 126.4, 127.6, 129.2, 129.8, 130.0, 131.7, 132.6, 134.2, 135.5, 137.4. NIR-IR (KBr cm^-1) 3060, 2956, 2925, 2898, 2854, 2158 (C≡C), 1601, 1458, 1251, 1105, 1071, 996, 949, 897, 859, 842, 814, 759, 707, 644, 534, 459, 423.