Cesium carbonate → Ethyl 7-(4-(2-(1-acetylindolin-5-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate

HRID 535650

반응식

HRID 535650 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Br[C:42]1[C:50]2[O:49][C:48]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[CH:47][C:46]=2[CH:45]=[CH:44][CH:43]=1.[N:56]1([CH2:62][CH2:63][C:64]2[CH:65]=[C:66]3[C:70](=[CH:71][CH:72]=2)[N:69]([C:73](=[O:75])[CH3:74])[CH2:68][CH2:67]3)[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]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]>[C:73]([N:69]1[C:70]2[C:66](=[CH:65][C:64]([CH2:63][CH2:62][N:56]3[CH2:61][CH2:60][N:59]([C:42]4[C:50]5[O:49][C:48]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[CH:47][C:46]=5[CH:45]=[CH:44][CH:43]=4)[CH2:58][CH2:57]3)=[CH:72][CH:71]=2)[CH2:67][CH2:68]1)(=[O:75])[CH3:74]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 46738833Ethyl 7-bromobenzofuran-2-carboxylateHCID 596367471-(5-(2-(Piperazin-1-yl)ethyl)indolin-1-yl)ethanone

생성물 1

HCID 59636756Ethyl 7-(4-(2-(1-acetylindolin-5-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate수율 61.5%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
95 °C

실험 절차

Cesium carbonate (0.724 g, 2.22 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.081 g, 0.17 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.078 g, 0.09 mmol) were added under argon to a mixture of ethyl 7-bromobenzofuran-2-carboxylate (0.460 g, 1.71 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.491 g, 1.79 mmol) (example 38c) in dry degassed dioxane (8 mL) and the reaction was heated at 95° C. over night. After cooling to room temperature, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by flash chromatography (DCM/MeOH 95/5) to give 0.485 g (61%) of the product.

후처리

  1. customin dry
  2. customdegassed dioxane (8 mL)
  3. temperatureAfter cooling to room temperature
  4. additionwater and DCM were added
  5. customthe layers separated
  6. extractionThe aq phase was extracted with DCM (3×)
  7. washThe combined organic phases were washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by flash chromatography (DCM/MeOH 95/5)

출처 및 근거

ORD 기록
ord-3830199987214ab39ba092e1b152b6df
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859534B2

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