反应详情

To a solution of 3-azidoacetylpyridine (800 mg, 4.94 mmol) in dioxane 10 mL was added 2-methyl-5-nitrophenyl isocyanate (880 mg, 4.94 mmol) (commercially available), and triphenylphosphine (1.29 g, 4.94 mmol). The reaction mixture was placed in an oil bath preheated to 100° C. and stirred for 30 min. After evaporation of the solvent under reduced pressure the residue was partitioned between 4N HCl (20 mL) and dichloromethane (20 mL). The aqueous layer was neutralized with 15% NaOH and extracted with dichloromethane (3×20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous MgSO4, concentrated. The residue was silica gel column chromatographed (dichloromethane/ethanol:97/3) to give the title compound as yellow micro crystals (1.14 g, 78%).

1. customThe reaction mixture was placed in an oil bath
2. custompreheated to 100° C.
3. customAfter evaporation of the solvent under reduced pressure the residue
4. customwas partitioned between 4N HCl (20 mL) and dichloromethane (20 mL)
5. extractionextracted with dichloromethane (3×20 mL)
6. washThe combined organic layers were washed with brine (20 mL)
7. dry with materialdried over anhydrous MgSO4
8. concentrationconcentrated
9. customchromatographed (dichloromethane/ethanol:97/3)