Reaktion #628254

Reaktionsgleichung

N-(2-iodo-4-nitrophenyl)methanesulfonamide

triethylamine

ethynylcyclohexane

EtOAc

→

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

Ausbeute 91.9%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.WAITThe reaction mixture was left
3. 3
   TemperaturAfter cooling to room temperature
4. 4
   Filtrationthe inorganic precipitate was filtered off
5. 5
   Sonstigethe solution was transferred into a separating funnel
6. 6
   Waschenwashed with NaHCO3 (saturated solution, 3×200 ml) and water (2×150 ml)
7. 7
   TrocknenThe organic phase was dried over Na2SO4
8. 8
   Sonstigethe solvent was removed by evaporation under reduced pressure
9. 9
   SonstigeThe so obtained crude product
10. 10
    Sonstigewas crystallized (isopropyl ether)

Vorschrift

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 (isopropyl ether) to give 2-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole (11.7 g)

Quelle