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

HRID 907088Notes

Reaction equation

HRID 907088 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]#[N:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:16](I)[CH3:17]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]#[N:13])=[CH:8][N:9]2[CH2:16][CH3:17])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 534011976-Methoxy-1H-indole-3-carbonitrile

Product 1

HCID 116441001-ethyl-6-methoxy-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-methoxy-1H-indole-3-carbonitrile (9.9 g, 57.6 mmol) in DMF (150 mL) was added NaH (60% dispersion in mineral oil, 3.45 g, 86.3 mmol). The reaction mixture was stirred for 15 min and then ethyl iodide (5.53 mL, 69.1 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was then diluted with H2O and extracted with EtOAc (2×). The organic phases were washed with H2O (3×) and saturated NaCl and then dried and concentrated to a semi-solid. The crude product was purified via column chromatography on silica gel (200 g) using CH2Cl2/hexanes (50-100%) as eluent to yield 6-methoxy-1-ethyl-1H-indole-3-carbonitrile as a tan solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with EtOAc (2×)
  3. washThe organic phases were washed with H2O (3×) and saturated NaCl
  4. customdried
  5. concentrationconcentrated to a semi-solid
  6. customThe crude product was purified via column chromatography on silica gel (200 g)

Sources & evidence

ORD record
ord-b15b24cd9f6d49b4a9b11ff7e6e272d5
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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