Methyl iodide → 6-ethoxy-1-ethyl-1H-indole-3-carbonitrile

HRID 502108Notes

Reaction equation

HRID 502108 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:13]#[N:14])=[CH:7][N:8]2[CH2:11][CH3:12])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].IC.[CH2:23](C(C)=O)[CH3:24]>O>[CH2:23]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:13]#[N:14])=[CH:7][N:8]2[CH2:11][CH3:12])=[CH:4][CH:3]=1)[CH3:24]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 594250606-hydroxy-1-ethyl-1H-indole-3-carbonitrile

Product 1

HCID 115937256-ethoxy-1-ethyl-1H-indole-3-carbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution 6-hydroxy-1-ethyl-1H-indole-3-carbonitrile (80 mg, 0.43 mmol) in 5 mL of methyl ethyl ketone is added anhydrous K2CO3 (71 mg, 0.52 mmol) and iodomethane (0.05 mL, 0.60 mmol). After stirring overnight at reflux, the reaction mixture is cooled, diluted with H2O and extracted with EtOAc (3×). The combined organic phases are dried and concentrated. Flash chromatography (CH2Cl2) gives 94 mg (100% S) of 6-ethoxy-1-ethyl-1H-indole-3-carbonitrile as a white wax.

Workup

  1. temperatureat reflux
  2. temperaturethe reaction mixture is cooled
  3. extractionextracted with EtOAc (3×)
  4. customThe combined organic phases are dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d03268cf90f4a7491333bbf39631bee
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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