Water → 2-cyclohexyl-5-nitro-1H-indole

HRID 541073Notes

Reaction equation

HRID 541073 reaction equation
[CH:1]1([C:7]2[N:8](S(C)(=O)=O)[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CCOC(C)=O>C1COCC1>[CH:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 672853302-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole

Product 1

HCID 672849682-cyclohexyl-5-nitro-1H-indoleYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing 2-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole (5.8 g; 18 mmol) in THF (50 ml), tetrabutylammonium fluoride (1M solution in THF; 18 ml; 18 mmol) was added dropwise. The reaction mixture was refluxed for 18 hours, then cooled to room temperature. Water (50 ml) and EtOAc (50 ml) were added, the biphasic solution was transferred into a separating funnel, the organic layer separated and dried over Na2SO4, and the solvent was removed by evaporation under reduced pressure. The residue was purified by flash chromatography on silica gel (n-hexane/EtOAc, n-hexane 100→480%) to give 2-cyclohexyl-5-nitro-1H-indole (3.2 g), which was used without any further purification.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was refluxed for 18 hours
  3. customthe biphasic solution was transferred into a separating funnel
  4. customthe organic layer separated
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (n-hexane/EtOAc, n-hexane 100→480%)

Sources & evidence

ORD record
ord-a04a2bae575847a6be49df2c745162ab
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Reaction notes

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