Potassium Carbonate → HCID 44549958, Verbindung

HRID 2382089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382089
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1I)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:3][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[NH:4][CH:1]=1

Komponenten

6

Edukt 2

HCID 11430Potassium CarbonateHCID 68555340Allyl-(2-iodo-4-trifluoromethyl-phenyl)-amine

Produkt 1

HCID 44549958HCID 44549958, VerbindungAusbeute 37,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of allyl-(2-iodo-4-trifluoromethyl-phenyl)-amine (1.75 g, 5.35 mmol), tetrabutylammonium chloride (1.68 g, 5.35 mmol), palladium acetate (120 mg, 0.54 mmol) and potassium carbonate (2.22 g, 16.0 mmol) in DMF (50 mL) is heated at 80° C. for 1.5 h. The reaction is quenched with water and extracted three times with DCM. The combined organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane to afford 3-methyl-5-trifluoromethyl-1H-indole (401 mg). 1H NMR (300 MHz, CDCl3): δ=8.09 (broad s, 1H), 7.90 (s, 1 H), 7.44 (s, 1H), 7.10 (s, 1H), 2.38 (s, 3H).

Aufarbeitung

  1. customThe reaction is quenched with water
  2. extractionextracted three times with DCM
  3. dry with materialThe combined organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-087997e9c5fa424bafb481f40de183ad
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258130B2

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