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

HRID 541074Notes

Reaction equation

HRID 541074 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-0d09e8711b034641b4dd0c57e80f4177
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Reaction notes

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