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

HRID 541072Notes

Reaction equation

HRID 541072 reaction equation
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

Participants

8

Reactant 4

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

Product 1

HCID 672853302-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indoleYield 91.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

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)

Workup

  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 (isopropyl ether)

Sources & evidence

ORD record
ord-3108c8f787074142b0c3bb1bfc034f23
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Reaction notes

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