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

HRID 907090Notes

Reaction equation

HRID 907090 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-hydoxy-1-ethyl-1H-indole-3-carbonitrile (80 mg, 0.43 mmol) in 5 mL of methyl ethyl ketone was added anhydrous K2CO3 (71 mg, 0.52 mmol) and iodomethane (0.05 mL, 0.60 mmol). After stirring overnight at reflux, the reaction mixture was cooled, diluted with H2O and extracted with EtOAc (3×). The combined organic phases were dried and concentrated. Flash chromatography (CH2Cl2) gave 94 mg (100%) of 6-ethoxy-1-ethyl-1H-indole-3-carbonitrile as a white wax.

Workup

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

Sources & evidence

ORD record
ord-a29be489d14b4fa282e66e713d1f7838
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

Loading…