Citric Acid → HCID 68959366, 화합물

HRID 2191813노트

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HRID 2191813 반응식
[NH2:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[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].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:33]1[CH:34]=[CH:35][C:36]2[S:40][CH:39]=[CH:38][C:37]=2[CH:41]=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:40]1[C:36]2[CH:35]=[CH:34][C:33]([NH:1][C:2]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][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:41][C:37]=2[CH:38]=[CH:39]1

참가 물질

10

반응물 5

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 27765785-Bromo-1-benzothiopheneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 68959354HCID 68959354, 화합물

생성물 1

HCID 68959366HCID 68959366, 화합물

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

To toluene 3.0 mL suspension of tert-butyl 2-amino-4-(4-(methanesulfonamido)phenyl)benzoate 0.12 g and cesium carbonate 0.27 g were added 5-bromobenzothiophene 0.14 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.9 mg, tris(dibenzylideneacetone)dipalladium(0) 3.0 mg and palladium acetate 1.5 mg at room temperature, 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, 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=2:1] to give tert-butyl 2-((benzothiophen-5-yl)amino)-4-(4-(methanesulfonamido)phenyl)benzoate.

후처리

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationwas filtrated
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-7612fd0d10e445029da1df02f16d5696
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08327467B2

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