Stannane, tributyl-1-cyclopenten-1-yl- → HCID 67273154, Verbindung

HRID 1020917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020917
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:21][CH3:22])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2I)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Sn]([C:37]1[CH2:41][CH2:40][CH2:39][CH:38]=1)(CCCC)CCCC)CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:21][CH3:22])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:37]2[CH2:41][CH2:40][CH2:39][CH:38]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 10915290Stannane, tributyl-1-cyclopenten-1-yl-HCID 67274065HCID 67274065, Verbindung

Produkt 1

HCID 67273154HCID 67273154, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To 539 mg (1.22 mmol) the iodo intermediate from step 2 in 5 mL dry DMF was added 43 mg (0.061 mmol, 5 mol %) of PdCl2(PPh3)2, followed by 870 mg (2.44 mmol, 2 eq) tributylstannylcyclopentene. The reaction was heated to 90° C. for 4 h, concentrated, dissolved in EtOAc and filtered through celite. The EtOAc layer was washed with H2O, aqueous NaCl solution, dried (MgSO4), and concentrated. The product was purified by silica gel chromatography (5-15% EtOAc/hexane) to yield 302 mgs of 1-benzenesulfonyl-2-cyclopent-1-enyl-4,5-dimethoxy-1H-indole (65%).

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutiondissolved in EtOAc
  3. filtrationfiltered through celite
  4. washThe EtOAc layer was washed with H2O, aqueous NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe product was purified by silica gel chromatography (5-15% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-36f3aa065efc46ad8123bbdb4e93d65c
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716493B2

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