Cesium carbonate → tert-butyl 2-((1-(tert-butoxycarbonyl)-1H-indol-5-yl)amino)-4-phenylbenzoate

HRID 2191713노트

반응식

HRID 2191713 반응식
[NH2:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:62]1[CH:63]=[C:64]2[C:68](=[CH:69][CH:70]=1)[N:67]([C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])[CH:66]=[CH:65]2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:74]([O:73][C:71]([N:67]1[C:68]2[C:64](=[CH:63][C:62]([NH:1][C:2]3[CH:14]=[C:13]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:12]=[CH:11][C:3]=3[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:70][CH:69]=2)[CH:65]=[CH:66]1)=[O:72])([CH3:77])([CH3:75])[CH3:76]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 2728482N-Boc-5-bromoindoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

생성물 1

HCID 68959368tert-butyl 2-((1-(tert-butoxycarbonyl)-1H-indol-5-yl)amino)-4-phenylbenzoate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

To toluene 3.0 mL suspension of tert-butyl 2-amino-4-phenylbenzoate 0.20 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 17 mg, tris(dibenzylideneacetone)dipalladium(0) 7 mg, palladium acetate 2 mg and cesium carbonate 0.48 g was added tert-butyl 5-bromoindol-1-carboxylate 0.55 g, and it was heated and refluxed for 8 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 washing with 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=20:1] to give tert-butyl 2-((1-(tert-butoxycarbonyl)-1H-indol-5-yl)amino)-4-phenylbenzoate.

후처리

  1. temperaturewas heated
  2. temperaturerefluxed for 8 hours
  3. filtrationinsoluble matter was filtrated
  4. additionethyl acetate and 10% citric acid aqueous solution were added to it
  5. customThe organic layer was separated
  6. washafter washing with saturated sodium chloride aqueous solution
  7. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-b8607b0e3981444aa2ba881516686341
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08327467B2

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