Reaktion #9322

Reaktionsgleichung

tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)carbamate

6-methyl-2,4-dimethoxyphenylboric acid

barium hydroxide octahydrate

ethyl acetate

→

title compound

Ausbeute 63.4%

tert-Butyl N-[7-(2,4-dimethoxy-6-methylphenyl)-2-methoxypyrazolo[1,5-a]pyridin-3-yl]carbamate

Ausbeute 63.4%

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 the obtained organic layer over anhydrous magnesium sulfate
5. 5
   Filtrationfiltering it
6. 6
   Einengenthe solvent was concentrated under reduced pressure
7. 7
   Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

After dissolving tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)carbamate (300 mg) in 1,2-dimethoxyethane (10 mL) and water (5 mL), 6-methyl-2,4-dimethoxyphenylboric acid (258 mg), tetrakis (triphenylphosphine)palladium (0) complex (203 mg) and barium hydroxide octahydrate (415 mg) 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 the obtained organic layer over anhydrous magnesium sulfate and filtering it, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (230 mg) was obtained from the n-hexane:ethyl acetate (5:1) fraction as a brown oil.

Quelle