Cesium carbonate → tert-butyl 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoate

HRID 2191721노트

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HRID 2191721 반응식
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:3]=1.[CH2:23]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH:24]=[CH2:25].C(=O)([O-])[O-].[Cs+].[Cs+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:26]1([CH2:23]/[CH:24]=[CH:25]/[C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:3]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 75027AllylcyclohexaneHCID 68956988Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

생성물 1

HCID 68964903tert-butyl 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoate

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

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온도
110 °C

실험 절차

To toluene 3.0 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20 g were added allylcyclohexane 0.17 mL, cesium carbonate 0.36 g, tetrabutylammonium bromide 53 mg and polymer-carried bis(acetato)triphenylphosphine palladium(II) 86 mg at room temperature, and it was stirred at 110° C. for 22 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution, saturated sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoate.

후처리

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationinsoluble matter was filtrated
  3. additionethyl acetate and 10% citric acid aqueous solution were added to it
  4. customThe organic layer was separated
  5. customcollected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter sequential washing with 10% citric acid aqueous solution, saturated sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution
  8. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-d95569c415a94a17a8ae2274a8e6729f
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08327467B2

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