Piperazine, 2-pyridylethyl- → 5-Methoxy-N,N-dimethyl-7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxamide

HRID 535680

Reaktionsgleichung

Reaktionsgleichung von HRID 535680
Br[C:2]1[C:10]2[O:9][C:8]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:7][C:6]=2[CH:5]=[C:4]([O:16][CH3:17])[CH:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[CH3:17][O:16][C:4]1[CH:3]=[C:2]([N:29]2[CH2:30][CH2:31][N:26]([CH2:25][CH2:24][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=3)[CH2:27][CH2:28]2)[C:10]2[O:9][C:8]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:7][C:6]=2[CH:5]=1

Komponenten

8

Edukt 4

HCID 566605Piperazine, 2-pyridylethyl-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 596367447-Bromo-5-methoxy-N,N-dimethylbenzofuran-2-carboxamide

Produkt 1

HCID 596367115-Methoxy-N,N-dimethyl-7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

7-Bromo-5-methoxy-N,N-dimethylbenzofuran-2-carboxamide (0.20 g, 0.67 mmol), 1-(2-pyridin-2-yl-ethyl)piperazine (0.13 g, 0.67 mmol), Pd2 dba3 (0.031 g, 0.030 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (0.032 g, 0.070 mmol) and sodium t-butoxide (0.14 g, 1.41 mmol) were heated in toluene (1 mL) at 100° C. for 2 h. The mixture was allowed to cool. Ethyl acetate was added and the mixture was filtered through a pad of celite. The filtrate was washed with water and brine, dried over MgSO4 and the solvent was removed by rotary evaporation. The crude product was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-3%) to give the title compound. Yield: 0.14 g (52%).

Aufarbeitung

  1. temperatureto cool
  2. filtrationthe mixture was filtered through a pad of celite
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed by rotary evaporation
  6. customThe crude product was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-3%)

Quellen und Nachweise

ORD-Eintrag
ord-e8ee74b43f8e49dc9f0fc656bba9c955
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859534B2

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