反应详情

温度

90 °C

To a stirred solution of compound 2 (0.300 g, 0.790 mmol, 1.00 equiv) in 1,4-dioxane (10 mL) were added 4-fluorobenzylamine (0.200 g, 1.58 mmol, 2.00 equiv), Cs2CO3 (0.500 g, 1.50 mmol, 2.00 equiv) followed by Pd2 (dba)3 (0.072 g, 0.079 mmol, 10 mol %) and Xantphos (0.045 g, 0.079 mmol, 10 mol %) at RT. The reaction mixture was heated at 90° C. and stirred at the same temperature for 8 h. After consumption of the starting material (by TLC), the reaction mixture was concentrated under vacuum. The obtained residue was diluted with water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The crude material was purified by silica gel column chromatography (EtOAc/Hexane 2:23) to afford compound 3 (0.140 g, 50.3%) as yellow solid. TLC: 40% EtOAc/Hexane (Rf: 0.25); 1H NMR (500 MHz, CDCl3): δ 7.31-7.28 (m, 2H), 7.06 (t, J=8.5 Hz, 1H), 7.00 (s, 2H), 6.91 (br s, 1H), 6.60 (d, J=9.5 Hz, 1H), 4.46 (br s, 1H), 4.31 (d, J=4.4 Hz, 2H), 4.20 (q, J=7.0 Hz, 2H), 1.28 (t, J=7.0 Hz, 3H); LC-MS: m/z=350 (M+-1) at RT 3.69 (97.8% purity).

1. customAfter consumption of the starting material (by TLC)
2. concentrationthe reaction mixture was concentrated under vacuum
3. additionThe obtained residue was diluted with water (50 mL)
4. extractionextracted with EtOAc (2×50 mL)
5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe crude material was purified by silica gel column chromatography (EtOAc/Hexane 2:23)