Reaction #9310

Reaction equation

Water

cyclopropylmethyl bromide

N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(2-oxetanylmethyl)amine

sodium hydride

→

title compound

N-Cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(2-oxetanylmethyl)amine

Solvents

ethyl acetate

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturewhile cooling on ice
3. 3
   Washthe extract was washed with 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 silica gel column chromatography

Procedure

After dissolving N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(2-oxetanylmethyl)amine (8 mg) in N,N-dimethylformamide (2 mL), sodium hydride (60%, 1.6 mg) was added while cooling on ice, and then cyclopropylmethyl bromide (3.8 μL) was added and the mixture was stirred at room temperature for 12 hours. Water was added to the reaction mixture, extraction was performed with ethyl acetate and the extract was washed with 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 (1.8 mg) was obtained from the n-hexane:ethyl acetate (10:1) fraction as a yellow oil.

Source