Reaktion #66754

Reaktionsgleichung

tert-Butyl 6-bromo-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

water

→

compound

tert-Butyl 6-(1-Methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate

Lösungsmittel

—

solution

dioxane

Na2CO3

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Sonstigedegassed
3. 3
   SonstigeThe reaction liquid
4. 4
   Temperaturcooled to room temperature
5. 5
   Filtrationfiltered through Celite
6. 6
   ExtraktionThe filtrate was extracted with chloroform
7. 7
   Trocknenthe organic layer was dried with sodium sulfate
8. 8
   SonstigeSodium sulfate was removed through filtration
9. 9
   Einengenthe filtrate was concentrated under reduced pressure
10. 10
    Sonstigethe residue was purified through silica gel column chromatography (hexane/EtOAc)

Vorschrift

tert-Butyl 6-bromo-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate (1 g) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (682 mg) were dissolved in dioxane in a nitrogen atmosphere, and aqueous 2M Na2CO3 (10 ml) solution (3.8 mL) and tetrakis(triphenylphosphine)palladium (144 mg) were added thereto, and degassed. The reaction liquid was stirred overnight at 100° C., cooled to room temperature, then water was added thereto, and filtered through Celite. The filtrate was extracted with chloroform, and the organic layer was dried with sodium sulfate. Sodium sulfate was removed through filtration, the filtrate was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/EtOAc) to obtain the intended compound as a pale yellow solid.

Quelle