Reaction Steps
A mixture of 3′-ethoxy-4′-methoxybiphenyl-3-carboxylic acid (0.55 g, 2.0 mmol) and CDI (0.39 g, 2.4 mmol) in DMF (30 mL) was stirred at ambient temperature under nitrogen for 90 minutes. 4-aminomethyl-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione hydrochloride (0.65 g, 2.0 mmol) and triethylamine (0.61 g, 6.0 mmol) were added, and the mixture was allowed to stir for 3 hours. The mixture was poured into water (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic phases were washed with water (3×150 mL), dried (MgSO4), and evaporated, providing 0.75 g of the product as a pale yellow solid (69% yield): mp 196-198° C.; 1H NMR (DMSO-d6) δ 1.36 (t, J=6.9 Hz, 3H), 2.05-2.10 (m, 1H), 2.54-2.64 (m, 2H), 2.85-2.98 (m, 1H), 3.83 (s, 3H), 4.18 (q, J=6.3 Hz, 2H), 5.02 (d, J=6.3 Hz, 2H), 5.20 (dd, J=12.7 Hz, d=5.4 Hz, 1H), 7.06 (d, J=8.5 Hz, 1H), 7.74-7.83 (m, 4H), 7.87-7.94 (m, 2H), 8.03 (t, J=7.8 Hz, 1H), 8.16 (d, J=7.7 Hz, 1H), 9.56 (t, J=6.3 Hz, 1H), 11.18 (s, 1H); 13C NMR (DMSO-d6) δ 14.8, 22.0, 31.0, 38.6, 49.0, 55.5, 64.0, 111.8, 119.8, 120.0, 122.0, 122.4, 127.3, 130.1, 131.7, 133.3, 134.9, 138.6, 139.1, 148.2, 149.2, 150.5, 155.1, 164.5, 167.0, 167.8, 169.8, 172.7; Anal. calcd for C29H26N4O7.0.5H2O: C, 63.15; H, 4.93; N, 10.16. Found: C, 63.36; H, 4.80; N, 10.19.
