反应详情

To a stirred solution of 4-amino-3-methylpyridine (160 mg) in dimethylformamide (10 ml) under an atmosphere of nitrogen was added sodium hexamethyldisilazide (1.0M solution in tetrahydrofuran, 1.5 ml). The reaction mixture was stirred at room temperature for 10 minutes. 2-Cyclopropanecarbonyl-7-methoxy-benzofuran-4-carboxylic acid 4-nitrophenyl ester (280 mg) was then added and stirring continued for 18 h. Water (10 ml) was added and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (150 ml), washed with water (3×50 ml) and washed with brine (50 ml). The combined aqueous layers were extracted with dichloromethane (2×50 ml), the organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 5% methanol in dichloromethane followed by trituration with diethyl ether afforded the title compound as an off-white solid (130 mg).

1. stirringstirring
2. waitcontinued for 18 h
3. customthe solvent was removed in vacuo
4. dissolutionThe residue was dissolved in ethyl acetate (150 ml)
5. washwashed with water (3×50 ml)
6. washwashed with brine (50 ml)
7. extractionThe combined aqueous layers were extracted with dichloromethane (2×50 ml)
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customPurification by flash chromatography on silica eluting with 5% methanol in dichloromethane