Iodoethane → 2-cyclohexyl-1-ethyl-5-nitro-1H-indole

HRID 1947433Notes

Reaction equation

HRID 1947433 reaction equation
[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)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:19](I)[CH3:20]>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH:1]1([C:7]2[N:8]([CH2:19][CH3:20])[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

5

Reactant 2

HCID 6340IodoethaneHCID 672849682-cyclohexyl-5-nitro-1H-indole

Product 1

HCID 672850022-cyclohexyl-1-ethyl-5-nitro-1H-indoleYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-cyclohexyl-5-nitro-1H-indole (5 g; 20.5 mmol) in DMF (100 ml) sodium hydride (50% suspension) (1 g, 20.5 mmol) was added; the mixture was left under stirring for 30 minutes, then ethyl iodide (2.5 ml; 30.8 mmol) in DMF (10 ml) was added dropwise and the resulting mixture was left under stirring at room temperature for 18 hours. The reaction mixture was poured in NaHCO3 (saturated solution, 100 ml) and stirred for 30 minutes. The solid was filtered under vacuum to give 2-cyclohexyl-1-ethyl-5-nitro-1H-indole (4.8 g) which was used without any further purification.

Workup

  1. waitthe mixture was left
  2. waitthe resulting mixture was left
  3. stirringunder stirring at room temperature for 18 hours
  4. stirringstirred for 30 minutes
  5. filtrationThe solid was filtered under vacuum

Sources & evidence

ORD record
ord-8a3668fd56984fee803026ebbb593be9
Source dataset
uspto-grants-2013_03
Patent number
US08399477B2

Reaction notes

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