反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
N-(3-Amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (75 mg, 0.266 mmol, 1 equiv.) was dissolved in 20 mL dichloromethane and 20 mL of saturated aqueous NaHCO3 solution was added. The biphasic mixture was cooled to 0° C. and phosgene (˜2 M solution in toluene, 0.44 mL) was added to the organic layer via syringe in one portion without stirring. The mixture was then stirred vigorously for 10 min, then the layers were separated. The aqueous layer was extracted once with dichloromethane and the combined organics were dried (Na2SO4), filtered and most of the dichloromethane was removed in vacuo, leaving the toluene. To this isocyanate residue was then added 1-(4-aminonaphthalen-1-yl)pyrrolo[3,2-c]pyridine (Example 1) (46 mg, 0.177 mmol, 1 equiv.) dissolved in 5 mL anhydrous THF. The mixture was left to stir at room temperature overnight, then the solvents were removed in vacuo. The residue was purified by column chromatography on SiO2 using dichloromethane/MeOH eluent mixtures. The title compound (34 mg) was isolated as a pink foam.
WORKUP
后处理
- stirringThe mixture was then stirred vigorously for 10 min
- customthe layers were separated
- extractionThe aqueous layer was extracted once with dichloromethane
- dry with materialthe combined organics were dried (Na2SO4)
- filtrationfiltered and most of the dichloromethane
- customwas removed in vacuo
- customleaving the toluene
- waitThe mixture was left
- stirringto stir at room temperature overnight
- customthe solvents were removed in vacuo
- customThe residue was purified by column chromatography on SiO2