Cyclopropylacetylene → 2-cyclopropyl-1H-indole

HRID 1092413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1092413
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[CH3:10].[CH:12]1(C#C)[CH2:14][CH2:13]1>O1CCOCC1.CN(C)C(N(C)C)=N.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.[Cu]I>[CH:12]1([C:9]2[NH:8][C:3]3[C:4]([CH:10]=2)=[CH:5][CH:6]=[CH:7][CH:2]=3)[CH2:14][CH2:13]1

Komponenten

7

Edukt 2

HCID 138823CyclopropylacetyleneHCID 1405592'-Iodoacetanilide

Produkt 1

HCID 113895272-cyclopropyl-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel2×HCID 664601,1,3,3-TetramethylguanidineLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of N-(2-iodophenyl)acetamide (100 mg, 0.38 mmol) in dioxane (750 mL) and 1,1,3,3-tetramethylguanidine (750 mL) was added cyclopropylacetylene (41 mL, 0.49 mmol), bis(triphenylphosphine)palladium(II) chloride (35 mg, 0.05 mmol), and copper(I) iodide (10 mg, 0.05 mmol). The reaction was stirred overnight at 80° C. The solution was cooled and partitioned between water and methylene chloride. The organic layer was dried (MgSO4) and concentrated to give the uncyclized Sonagashira coupling product. Dioxane (750 mL) and 1,1,3,3-tetramethylguanidine (750 mL) were added and the reaction was stirred overnight at 90° C. The solution was again partitioned between water and methylene chloride. The organic layer was dried (MgSO4) and concentrated to give the desired indole, which was used without further purification.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. custompartitioned between water and methylene chloride
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customto give the uncyclized Sonagashira coupling product
  6. stirringthe reaction was stirred overnight at 90° C
  7. customThe solution was again partitioned between water and methylene chloride
  8. dry with materialThe organic layer was dried (MgSO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f0e01993e9cc482989ec6949774b58fd
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129424B2

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