Reaction Steps
The white crystal (3.7 g, 11.83 mmol) from step 1 mixed with Herrmann's palladacycle (0.166 g, 0.18 mmol), [(t-Bu)PH]BF4(0.206 g, 0.71 mmol), cesium carbonate (3.87 g, 11.82 mmol), and DBU (0.18 mL, 1.20 mmol) in DMF (30 mL) under Ar was added with 4-(carbomethoxy)phenylboronic acid (2.17 g, 11.82 mmol). The reaction mixture was irradiated with microwave 120 W to reflux for 20 min. After irradiation, the resulting mixture was evaporated to get oil residue. The residue suspended in EA (50 mL) was washed with water (3×50 mL). The EA layer dried over MgSO4 was evaporated to give title compound as beige solid (2.57 g, 52.7%). Rf=0.11 (EA/Hexane=1:4); 1H NMR (400 MHz, CDCl3) δ 1.14 (t, J=7.2 Hz, 3H), 2.62 (q, J=7.2 Hz, 2H), 2.97 (dd, J=7.6 Hz, 2H), 4.23 (dd, J=7.6 Hz, 2H), 7.18-7.27 (m, 5H), 7.45 (t, J=7.6 Hz, 1H), 7.69-7.71 (m, 2H), 7.74 (dd, J=7.6 and 1.2 Hz, 1H), 8.03-8.05 (m, 2H), 8.28 (dd, J=8.0 and 1.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 10.7, 28.0, 34.7, 45.3, 52.1, 121.2, 126.2, 126.9 (2C), 127.2, 128.7, 128.83, 128.85, 128.9, 130.2, 130.7, 134.8, 137.5, 138.0, 143.2, 144.3, 156.4, 162.3, 167.2;
