Iodoethane → 6-ethoxy-1-ethyl-1H-indole-3-carbonitrile

HRID 1009519Notes

Reaction equation

HRID 1009519 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+].I[CH2:22][CH3:23]>C(C(C)=O)C.O>[CH2:22]([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)[CH3:23]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 594250606-hydroxy-1-ethyl-1H-indole-3-carbonitrile

Product 1

HCID 115937256-ethoxy-1-ethyl-1H-indole-3-carbonitrileYield 102%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

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 iodoethane (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%) 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-ae71b342f082449f85d420bca979b894
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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