反应详情

温度

110 °C

3-Bromo-5-chloropyridin-2-amine (50.0 g, 241 mmol), phenol (45.4 g, 482 mmol), copper(I)oxide (1.72 g, 12.1 mmol), (E)-2-hydroxybenzaldehyde oxime (6.61 g, 48.2 mmol), Cs2CO3 (157 g, 482 mmol), and 3A powdered molecular (72.3 g) sieves were placed in DMF (300 mL) and heated at 110° C. for 3 days. Reaction was cooled, then filtered through celite. Reaction was then partitioned between water and ether. An emulsion was formed and was filtered through a plug of celite. Water was extracted with ether then dried, filtered, and concentrated. Crude material was purified on a first silica gel chromatography (5-10% EtOAc in hexanes), and then on a second column to provide the title compound (8.00 g, 15.0% yield). 1H NMR (CDCl3) δ 7.80 (d, 1H), 7.39 (t, 2H), 7.19 (t, 1H), 7.03 (d, 2H), 6.94 (d, 1H), 4.76 (bs, 2H); Mass spectrum (apci) m/z=221 (100).

1. customReaction
2. temperaturewas cooled
3. filtrationfiltered through celite
4. customReaction
5. customwas then partitioned between water and ether
6. customAn emulsion was formed
7. filtrationwas filtered through a plug of celite
8. extractionWater was extracted with ether
9. customthen dried
10. filtrationfiltered
11. concentrationconcentrated
12. customCrude material was purified on a first silica gel chromatography (5-10% EtOAc in hexanes)