Reaktion #9306

Reaktionsgleichung

sodium hydroxide

1-iodopropane

hydrochloric acid ethyl acetate

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

sodium hydride

→

title compound

N-[7-(2,4-Dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]-N-propylamine

Lösungsmittel

N,N-dimethylformamide

ethyl acetate

Water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturwhile cooling on ice
3. 3
   Waschenthe extract was washed with brine
4. 4
   TrocknenThe obtained organic layer was dried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   Sonstigeto obtain a crude product
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hours
9. 9
   Temperaturwhile cooling on ice
10. 10
    Extraktionextraction
11. 11
    Waschenthe organic layer was washed with water and brine
12. 12
    TrocknenAfter drying over anhydrous magnesium sulfate and filtration
13. 13
    Einengenthe solvent was concentrated under reduced pressure
14. 14
    Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

After dissolving tert-butyl N-[7-(2,4-dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate (150 mg) in N,N-dimethylformamide (3 mL), sodium hydride (60%, 21 mg) was added while cooling on ice, and then 1-iodopropane (0.041 mL) was added and the mixture was stirred for 30 minutes. 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 distilled off 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 (4 mL) was added, and the mixture was stirred at room temperature for 2 hours. 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 (60 mg) was obtained from the n-hexane:ethyl acetate (20:1) fraction as a yellow oil.

Quelle