Reacción #9297

Ecuación de reacción

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

propionaldehyde

sulfuric acid

sodium borohydride

→

title compound

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

Disolventes

diethyl ether

Water

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added in five portions
2. 2
   workup.STIRRINGstirring
3. 3
   Lavadothe extract was washed with saturated aqueous sodium hydrogencarbonate and brine
4. 4
   SecadoAfter drying over anhydrous magnesium sulfate and filtration
5. 5
   Concentraciónthe solvent was concentrated under reduced pressure
6. 6
   Otrothe residue was purified by preparative TLC [n-hexane:ethyl acetate (5:1), Rf=0.5]

Procedimiento

N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(2-methoxyethyl)amine (14 mg) was dissolved in tetrahydrofuran (1 mL), and after adding propionaldehyde (0.016 mL) and 3 M aqueous sulfuric acid (0.77 mL), sodium borohydride (5.8 mg) was added in five portions while vigorously stirring on ice, and stirring was continued for 30 minutes. Water was added to the reaction mixture, extraction was performed with diethyl ether and the extract was washed with saturated aqueous sodium hydrogencarbonate and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure and the residue was purified by preparative TLC [n-hexane:ethyl acetate (5:1), Rf=0.5] to obtain the title compound (9.5 mg) as a light yellow oil.

Fuente