反応 #9296

反応方程式

sodium hydroxide

2-bromoethyl methyl ether

hydrochloric acid ethyl acetate

tert-butyl N-[7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]carbamate

sodium hydride

→

title compound

N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(2-methoxyethyl)amine

溶媒

N,N-dimethylformamide

ethyl acetate

Water

ethyl acetate

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度while cooling on ice
3. 3
   洗浄the extract was washed with brine
4. 4
   乾燥The obtained organic layer was dried over anhydrous magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮the solvent was concentrated under reduced pressure
7. 7
   その他to obtain a crude product
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hour
9. 9
   温度while cooling on ice
10. 10
    抽出extraction
11. 11
    洗浄the organic layer was washed with water and brine
12. 12
    乾燥After drying over anhydrous magnesium sulfate and filtration
13. 13
    濃縮the solvent was concentrated under reduced pressure
14. 14
    その他the residue was purified by silica gel column chromatography

実験手順

After dissolving tert-butyl N-[7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]carbamate (57 mg) in N,N-dimethylformamide (2 mL), sodium hydride (60%, 7.3 mg) was added while cooling on ice, and then 2-bromoethyl methyl ether (0.015 mL) was added and the mixture was stirred for 1 hour. Water was added to the reaction mixture, extraction was performed with ethyl acetate and the extract was washed with brine. The obtained organic layer was dried over anhydrous magnesium sulfate and filtered, and then the solvent was concentrated under reduced pressure to obtain a crude product. This was dissolved in ethyl acetate (1 mL) without purification, a 4 N hydrochloric acid/ethyl acetate solution (2 mL) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with 5 N aqueous sodium hydroxide while cooling on ice, and then extraction was performed with ethyl acetate and the organic layer was washed with water and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (46 mg) was obtained from the n-hexane:ethyl acetate (5:1) fraction as a yellow oil.

出典