反应详情

2-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine (187 mg) was dissolved in tetrahydrofuran (4 ml) under a nitrogen atmosphere, and then triethylamine (0.21 ml) and phenyl chloroformate (0.188 ml) were added dropwise thereto while cooling in an ice bath, followed by stirring at room temperature for 20 min. To the reaction mixture were added N,N-dimethylformamide (2 ml) and 4-(pyrrolidin-1-yl)piperidine (609 mg) at room temperature, followed by stirring overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, to which methanol (10 ml)-tetrahydrofuran (10 ml) was added to dissolve, and then 10% palladium carbon (200 mg) was added thereto under a nitrogen atmosphere, followed by replacing with hydrogen inside the system and stirring overnight. After replacing with nitrogen inside the system, the catalyst was filtered and washed with ethanol. The filtrate was concentrated under a reduced pressure to give a residue, which was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate, then ethyl acetate:methanol=95:5) to provide the titled compound (214 mg, 71%) as colorless crystals.

1. temperaturewhile cooling in an ice bath
2. stirringby stirring overnight
3. customThe reaction mixture was partitioned between ethyl acetate and water
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated under a reduced pressure
7. customto give a residue
8. dissolutionto dissolve
9. stirringstirring overnight
10. filtrationthe catalyst was filtered
11. washwashed with ethanol
12. concentrationThe filtrate was concentrated under a reduced pressure
13. customto give a residue, which
14. customwas purified by silica gel column chromatography (Fuji Silysia NH, eluent