Cesium carbonate → Tert-butyl 2-((benzofuran-5-yl)amino)-4-phenethylbenzoate

HRID 2191704

반응식

HRID 2191704 반응식
[NH2:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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:64]1[CH:65]=[CH:66][C:67]2[O:71][CH:70]=[CH:69][C:68]=2[CH:72]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[O:71]1[C:67]2[CH:66]=[CH:65][C:64]([NH:1][C:2]3[CH:14]=[C:13]([CH2:15][CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:12]=[CH:11][C:3]=3[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:72][C:68]=2[CH:69]=[CH:70]1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 90015Benzofuran, 5-bromo-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl3회HCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

생성물 1

HCID 68958873Tert-butyl 2-((benzofuran-5-yl)amino)-4-phenethylbenzoate

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매3회HCID 1140Toluene용매

실험 절차

To toluene 3.0 mL suspension of tert-butyl 2-amino-4-phenethylbenzoate 0.10 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8 mg, tris(dibenzylideneacetone)dipalladium(0) 3 mg and cesium carbonate 0.22 g was added 5-bromobenzofuran 0.19 g, and it was heated and refluxed for 24 hours. After the reaction mixture was cooled to room temperature, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8 mg and tris(dibenzylideneacetone)dipalladium(0) 3 mg were added to it, and it was heated and refluxed for 24 hours. After the reaction mixture was cooled to room temperature, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8.0 mg and tris(dibenzylideneacetone)dipalladium(0) 3 mg were added to it, and it was heated and refluxed for 24 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-((benzofuran-5-yl)amino)-4-phenethylbenzoate. Trifluoroacetic acid 3.0 mL was added to the obtained tert-butyl 2-((benzofuran-5-yl)amino)-4-phenethylbenzoate, and it was stirred at room temperature for 3 hours. 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:acetic acid=30:10:1] to give 2-((benzofuran-5-yl)amino)-4-phenethylbenzoic acid 21 mg of white solid.

후처리

  1. temperaturewas heated
  2. temperaturerefluxed for 24 hours
  3. temperaturewas heated
  4. temperaturerefluxed for 24 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. temperaturewas heated
  7. temperaturerefluxed for 24 hours
  8. temperatureAfter the reaction mixture was cooled to room temperature
  9. filtrationinsoluble matter was filtrated
  10. additionethyl acetate and 10% citric acid aqueous solution were added to it
  11. customThe organic layer was separated
  12. customcollected
  13. dry with materialdried over anhydrous magnesium sulfate
  14. washafter washing with saturated sodium chloride aqueous solution
  15. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-d41864d5629d4ca9aeeb0623220e9411
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08327467B2

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