Triethylamine → 2-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole

HRID 1947431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947431
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].C(N(CC)CC)C.[C:23]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)#[CH:24].CCOC(C)=O>CN(C=O)C.[Cu]I.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>[CH:25]1([C:23]2[N:11]([S:12]([CH3:15])(=[O:14])=[O:13])[C:3]3[C:2]([CH:24]=2)=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][CH:4]=3)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 70263EthynylcyclohexaneHCID 67284366N-(2-iodo-4-nitrophenyl)methanesulfonamide

Produkt 1

HCID 672853302-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indoleAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture containing N-(2-iodo-4-nitrophenyl)methanesulfonamide (13.5 g; 39.5 mmol), triethylamine (17.9 ml; 129 mmol), ethynylcyclohexane (8.55 g; 79 mmol) in DMF (60 ml), CuI (1.5 g; 7.9 mmol) and dichlorobis(triphenylphosphine)palladium(II) [Cl2(PPh3)2Pd] (2.77 g; 3.95 mmol) were added. The reaction mixture was left under stirring at 70° C. for 18 hours. After cooling to room temperature, EtOAc (100 ml) was added, the inorganic precipitate was filtered off and the solution was transferred into a separating funnel and washed with NaHCO3 (saturated solution, 3×200 ml) and water (2×150 ml). The organic phase was dried over Na2SO4, the solvent was removed by evaporation under reduced pressure. The so obtained crude product was crystallized (isopropylether) to give 2-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole (11.7 g)

Aufarbeitung

  1. additionwere added
  2. waitThe reaction mixture was left
  3. temperatureAfter cooling to room temperature
  4. filtrationthe inorganic precipitate was filtered off
  5. customthe solution was transferred into a separating funnel
  6. washwashed with NaHCO3 (saturated solution, 3×200 ml) and water (2×150 ml)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. customthe solvent was removed by evaporation under reduced pressure
  9. customThe so obtained crude product
  10. customwas crystallized (isopropylether)

Quellen und Nachweise

ORD-Eintrag
ord-61152ca3bce84b399847d4ac6bc6eebb
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399477B2

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