Reaktion #9298

Reaktionsgleichung

N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethyl-N-tetrahydro-3-furanylmethylamine

2,4-dimethoxy-6-methylphenylboric acid

barium hydroxide octahydrate

ethyl acetate

→

title compound

Ausbeute 49.4%

N-Cyclopropylmethyl-N-[7-(2,4-dimethoxy-6-methylphenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-tetrahydro-3-furanylmethylamine

Ausbeute 49.4%

Lösungsmittel

1,2-dimethoxyethane

water

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturthe mixture was heated
3. 3
   Waschenthe organic layer was washed with brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenthe solvent was concentrated under reduced pressure
7. 7
   SonstigeThe obtained residue was purified by silica gel column chromatography

Vorschrift

After dissolving N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethyl-N-tetrahydro-3-furanylmethylamine (150 mg) in 1,2-dimethoxyethane (20 mL) and water (10 mL), 2,4-dimethoxy-6-methylphenylboric acid (155 mg), tetrakis(triphenylphosphine)palladium (0) complex (92 mg) and barium hydroxide octahydrate (250 mg) were added and the mixture was heated and stirred at 80° C. for 1 hour. Water was added to the reaction mixture, extraction was performed with ethyl acetate, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and the title compound (88 mg) was obtained from the n-hexane:ethyl acetate (6:1) fraction as a yellow oil.

Quelle