反应详情

A solution of 3-iodo-5-nitropyridin-2-ol (2.66 g, 10.0 mmol) in THF (30 mL) was cooled to −20° C. NaH (60% dispersion in mineral oil, 0.600 g, 15.0 mmol) was added cautiously in three portions. After being stirred for 30 min at this temperature, methyl iodide (6.23 mL, 100.0 mmol) was added dropwise through a syringe. The resulting mixture was allowed to warm to rt during a 30 min period. Stirring was continued for 18 h at rt. Water (15 mL) was added with caution to quench the reaction. THF was removed under reduced pressure and methylene chloride (80 mL) was added to the aqueous phase. Layers were separated and the aqueous phase was extracted with methylene chloride (2×50 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated to afford the desired product as a yellow crystalline solid. 1H-NMR (CDCl3, 400 MHz): δ=3.73 (s, 3H), 8.65 (d, J=2.8 Hz, 1H), 8.74 (d, J=2.8 Hz, 1H). MS (ES+): m/z 280.96 [MH+]. HPLC: tR=2.55 min (ZQ2000, polar—5 min).

1. additionwas added dropwise through a syringe
2. customto quench
3. customthe reaction
4. customTHF was removed under reduced pressure and methylene chloride (80 mL)
5. additionwas added to the aqueous phase
6. customLayers were separated
7. extractionthe aqueous phase was extracted with methylene chloride (2×50 mL)
8. dry with materialThe combined organic phases were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated