Citric Acid → HCID 68961151, 화합물

HRID 2191821노트

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HRID 2191821 반응식
[NH2:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:36]1[CH:37]=[CH:38][C:39]2[S:43][CH:42]=[CH:41][C:40]=2[CH:44]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>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.C(OCC)(=O)C.C1(C)C=CC=CC=1>[S:43]1[C:39]2[CH:38]=[CH:37][C:36]([NH:1][C:2]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]=4)[CH:12]=[CH:11][C:3]=3[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:44][C:40]=2[CH:41]=[CH:42]1

참가 물질

10

반응물 5

HCID 311Citric AcidHCID 10796Cesium carbonate2회HCID 27765785-Bromo-1-benzothiophene2회HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl3회HCID 68958545HCID 68958545, 화합물

생성물 1

HCID 68961151HCID 68961151, 화합물

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매3회HCID 9811564Bis(dibenzylideneacetone)palladium촉매3회HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

To toluene 3.0 mL suspension of tert-butyl 2-amino-4-(3-(tert-butoxycarbonyloxy)phenyl)benzoate 0.12 g and cesium carbonate 0.25 g were added 5-bromobenzothiophene 0.13 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.4 mg, tris(dibenzylideneacetone)dipalladium(0) 2.9 mg and palladium acetate 1.4 mg at room temperature, and it was stirred at 110° C. for 24 hours. 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.4 mg, tris(dibenzylideneacetone)dipalladium(0) 2.9 mg and palladium acetate 1.4 mg were added to it, and it was stirred at 110° C. for 21 hours. Cesium carbonate 51 mg, 5-bromobenzothiophene 33 mg, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.4 mg, tris(dibenzylideneacetone)dipalladium(0) 2.9 mg and palladium acetate 1.4 mg were added to it, and it was stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it, and insoluble matter was filtrated. 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=10:1] to give tert-butyl 2-((benzothiophen-5-yl)amino)-4-(3-(tert-butoxycarbonyloxy)phenyl)benzoate.

후처리

  1. stirringwas stirred at 110° C. for 21 hours
  2. stirringwas stirred at 110° C. for 24 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. filtrationwas filtrated
  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-8836dc27c4ef411597c74f9ef60d5307
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08327467B2

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