Reaktion #9303

Reaktionsgleichung

tert-butyl N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

4,6-dimethyl-2-methoxyphenylboric acid

barium hydroxide octahydrate

ethyl acetate

→

title compound

Ausbeute 102.9%

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

Ausbeute 102.9%

Lösungsmittel

1,2-dimethoxyethane

water

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturthe mixture was heated
3. 3
   Waschenthe extract was washed with brine
4. 4
   TrocknenAfter drying over anhydrous magnesium sulfate and filtration
5. 5
   Einengenthe solvent was concentrated under reduced pressure
6. 6
   Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

After dissolving tert-butyl N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate (2.0 g) in 1,2-dimethoxyethane (60 mL) and water (30 mL), 4,6-dimethyl-2-methoxyphenylboric acid (1.33 g), tetrakis(triphenylphosphine)palladium (0) complex (865 mg) and barium hydroxide octahydrate (2.34 g) were added and the mixture was heated and stirred at 80° C. for 3 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 (2.1 g) was obtained from the n-hexane:ethyl acetate (20:1) fraction as yellow amorphous.

Quelle