Reaction Steps
EDC hydrochloride (0.192 g, 1 mmol), m-anisic acid (0.152 g, 1 mmol) and triethylamine (0.14 mL, 2.5 mmol) were dissolved in dry DCM (10 mL). The reaction was stirred at room temperature for 30 min. Carbonitrile 4 (0.201 g, 1 mmol) dissolved in 5 mL dry DCM was added dropwise to the solution and reaction stirred for 18 h. The reaction was diluted with DCM (50 mL) and washed with 1M NaHSO4 (aq, 2×100 mL). Organics were dried over Na2SO4, filtered and solvent was removed under reduced pressure. The crude product was then purified by flash chromatography (4:1 hexane:ethyl acetate mobile phase) to produce a light yellow solid (Compound 22) in 73% yield. 1H NMR (400 MHz, CDCl3) δ 8.35 (s, 1H), 8.13 (s, 1H), 7.32 (s, 1H), 7.28 (s, 1H), 7.20 (d, J=7.5, 1H), 7.13 (t, J=7.8, 1H), 6.98 (s, 1H), 6.95 (d, J=8.1, 1H), 5.82 (s, 1H), 3.91 (q, J=5.3, 2H), 3.79-3.68 (m, 5H), 2.55 (s, 3H), 2.42 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 168.10, 159.87, 155.10, 144.27, 140.97, 136.27, 135.41, 129.42, 127.13, 124.48, 119.35, 119.23, 117.72, 116.87, 112.46, 94.30, 55.49, 43.39, 41.25, 29.92, 22.21, 18.57. IR (neat): 3380, 3357, 2957, 2925, 2217, 1605, 1583, 1535, 1258. ESI-LCMS m/z [M+H]+=375.18.
