[Synthesis]
4.3.8 Synthesis of 3-(3-aminophenyl)pyridine (3ha): m-Bromoaniline (0.5 mmol), base (1 mmol), cuprous iodide (20 mol%), 3-(1,1,1-tributylmethylstannyl)pyridine (0.75 mmol), and catalyst (1 mol%) were placed in a 10 mL vial protected by nitrogen and DMF (2 mL) was added to dissolve. ) was added to dissolve. The reaction mixture was heated to a specific temperature and reacted for 12 hours. Upon completion of the reaction, the reaction was quenched with water. The mixture was diluted with ethyl acetate (10 mL), filtered through a pad of diatomaceous earth and subsequently extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by rapid column chromatography on silica gel (eluent: ethyl acetate/hexane) to afford the target product 3-(3-aminophenyl)pyridine (3ha) as a yellow solid with a melting point of 69-70 °C. The residue was purified by fast column chromatography on silica gel (eluent: ethyl acetate/hexane).
Product characterization data:
1H NMR (400 MHz, CDCl3): δ = 8.80 (d, J = 1.44 Hz, 1H), 8.55 (d, J = 4.20 Hz, 1H), 7.81 (dt, J = 7.92, 1.68 Hz, 1H), 7.29-7.32 (m, 1H), 7.23 (t, J = 7.80 Hz, 1H), 6.93 (d , J = 7.64 Hz, 1H), 6.85-6.86 (m, 1H), 3.91 (s, 2H).
13C NMR (100 MHz, CDCl3): δ = 113.5, 114.7, 117.2, 123.5, 130.0, 134.3, 136.9, 138.8, 147.3, 148.1, 148.2. |