Reaktion #435014

Reaktionsgleichung

2,6-dimethoxy-4-(methoxymethyl)phenylboric acid

barium hydroxide octahydrate

7-bromo-2-ethyl-3-nitropyrazolo[1,5-a]pyridine

ethyl acetate

→

title compound

Ausbeute 56.0%

7-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-2-ethyl-3-nitropyrazolo[1,5-a]pyridine

Ausbeute 56.0%

Lösungsmittel

1,2-dimethoxyethane

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   SonstigeTo the resultant reaction mixture
3. 3
   Sonstigeremove insoluble residue
4. 4
   Filtrationwas filtered out with celite
5. 5
   ExtraktionThe filtrate was extracted with ethyl acetate
6. 6
   Extraktionthe organic extract
7. 7
   Waschenwas washed with brine
8. 8
   Trocknendried over anhydrous magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Sonstigethe solvent was evaporated under reduced pressure
11. 11
    SonstigeThe obtained residue was purified by silica gel column chromatography

Vorschrift

To a solution of 7-bromo-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (1.0 g) dissolved in a mixture of 1,2-dimethoxyethane (50 mL) and water (25 mL) was added 2,6-dimethoxy-4-(methoxymethyl)phenylboric acid (1.26 g), tetrakis(triphenylphosphine)palladium(0) (0.64 g) and barium hydroxide octahydrate (1.75 g), and the reaction mixture was heated and stirred for 2 hours at 80° C. To the resultant reaction mixture was added water and ethyl acetate, and remove insoluble residue was filtered out with celite. The filtrate was extracted with ethyl acetate, the organic extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography and the title compound (0.77 g) was obtained as yellow crystals from the n-hexane:ethyl acetate (3:1) fraction.

Quelle