반응 #66754

반응 방정식

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

용매

—

solution

dioxane

Na2CO3

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   기타degassed
3. 3
   기타The reaction liquid
4. 4
   온도cooled to room temperature
5. 5
   여과filtered through Celite
6. 6
   추출The filtrate was extracted with chloroform
7. 7
   건조the organic layer was dried with sodium sulfate
8. 8
   기타Sodium sulfate was removed through filtration
9. 9
   농축the filtrate was concentrated under reduced pressure
10. 10
    기타the residue was purified through silica gel column chromatography (hexane/EtOAc)

실험 절차

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.

출처