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

HRID 383822

反応式

HRID 383822 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
95 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2d5ff01034b24f9a9aa7cf399164cec2
出典データセット
uspto-grants-2013_02
特許番号
US08367676B2

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