Reaction #9297

Reaction equation

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

Solvents

diethyl ether

Water

tetrahydrofuran

Conditions

Workup

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

Procedure

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.

Source