反应详情

To a stirred solution 5-iodopyridin-2-ol (0.4 g, 1.80 mmol) in DME (10 mL) was added t-BuOK (0.604 g, 5.4 mmol). The mixture was stirred for 30 min at rt, K2CO3 (0.621 g, 4.5 mmol) and 2-iodopropane (0.35 mL, 3.6 mmol) were added, and the reaction was heated at reflux for about 3 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 60-120μ) using 10% ethyl acetate in hexane as eluent to afford 5-iodo-1-isopropylpyridin-2(1H)-one as an off-white solid (0.41 g, 67% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.90 (s, 1H), 7.49 (dd, 1H), 6.21 (d, 1H), 4.94 (t, 1H), 1.25 (t, 6H), LC-MS m/z calcd for [M+H]+ 263.98. found 264.0.

1. temperaturethe reaction was heated
2. temperatureat reflux for about 3 h
3. extractionextracted with ethyl acetate (2×100 mL)
4. washThe combined organic extracts were washed with brine solution (10 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under vacuum
7. customto obtain crude product
8. customThe crude product was purified by flash chromatography (silica gel, 60-120μ)