反应详情

温度

60 °C

To a suspension of sodium 5″-chloro-2,2′:5′,3″-terpyridine-3′-carboxylate (12-4, 3.12 g, 9.35 mmol, 1.0 equiv) in dimethylformamide (47 mL) was added 1-(5,6-dimethoxy-pyridin-2-yl)methanamine (5-6, 1.65 g, 9.82 mmol, 1.05 equiv), EDC (3.58 g, 18.7 mmol, 2.0 equiv), HOAt (2.55 g, 18.7 mmol, 2.0 equiv), and diisopropylethylamine (4.83 g, 37.4 mmol, 4.0 equiv) and the system was heated to 60° C. for 2 h. The reaction mixture was cooled and diluted with ethyl acetate (300 mL). The reaction mixture was washed with saturated sodium bicarbonate (2×100 mL), water (2×100 mL) and brine (1×100 mL), dried over magnesium sulfate and concentrated. The residue was purified via normal phase chromatography (10 to 100% EtOAc in hexanes, then 0 to 23% methanol in EtOAc, silica) to afford the desired product (12-5) as a white solid after concentration. 1H NMR (500 MHz, CDCl3) δ 8.95 (d, J=2.5 Hz, 1H), 8.80 (s, 1H), 8.66 (d, J=2.0 Hz, 1H), 8.38 (d, J=5.0 Hz, 1H), 8.26 (d, J=2.5 Hz, 1H), 8.04 (d, J=8.0 Hz, 1H), 7.96 (bs, 1H), 7.78 (t, J=3.0 Hz, 1H), 7.47 (bs, 1H), 7.23 (dd, J=7.5, 5.5 Hz, 1H), 7.01 (d, J=7.5 Hz, 1H), 6.85 (d, J=7.5 Hz, 1H), 4.55 (d, J=5.5 Hz, 2H), 3.88 (s, 3H), 3.83 (s, 3H). HRMS [M+H] C24H20ClN5O3 calc'd 462.1327. found 462.1332.

1. temperatureThe reaction mixture was cooled
2. washThe reaction mixture was washed with saturated sodium bicarbonate (2×100 mL), water (2×100 mL) and brine (1×100 mL)
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated
5. customThe residue was purified via normal phase chromatography (10 to 100% EtOAc in hexanes