反应详情

1-Isothiocyanato-4-(2,2,2-trifluoroethoxy)benzene (4.06 g) was dissolved in N,N-dimethylformamide (50 ml), and sodium hydride (60% in oil, 1.39 g) was added thereto under ice-cooling. Methyl 2-amino-6-chloropyridine-3-carboxylate (2.95 g) was dissolved in N,N-dimethylformamide (25 ml), the solution was added dropwise to the reaction mixture under ice-cooling, and the mixture was stirred for 20 min, and then at room temperature for 1 hr and 30 min. The reaction mixture was poured into 0.5M hydrochloric acid (80 ml), and the white precipitate was collected by filtration. The precipitate was dissolved in tetrahydrofuran (100 ml), and the solution was diluted with ethyl acetate (200 ml), washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a white residue. The residue was suspended in diethyl ether (100 ml), and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane), and washed with diethyl ether to give the white title compound (1.1 g).

1. temperatureunder ice-cooling
2. additionthe solution was added dropwise to the reaction mixture under ice-
3. temperaturecooling
4. waitat room temperature for 1 hr
5. custom30 min
6. filtrationthe white precipitate was collected by filtration
7. dissolutionThe precipitate was dissolved in tetrahydrofuran (100 ml)
8. additionthe solution was diluted with ethyl acetate (200 ml)
9. washwashed with saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customThe solvent was evaporated under reduced pressure
12. customto give a white residue
13. concentrationthe filtrate was concentrated under reduced pressure
14. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)
15. washwashed with diethyl ether