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

HRID 502106Notes

Reaction equation

HRID 502106 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) is added NaH (60% dispersion in mineral oil, 3.45 g, 86.3 mmol). The reaction mixture is stirred for 15 min and then ethyl iodide (5.53 mL, 69.1 mmol) is added and the mixture is stirred at room temperature overnight. The reaction mixture is then diluted with H2O and extracted with EtOAc (2×). The organic phases are washed with H2O (3×) and saturated NaCl and then dried and concentrated to a semi-solid. The crude product is 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 is stirred at room temperature overnight
  2. extractionextracted with EtOAc (2×)
  3. washThe organic phases are washed with H2O (3×) and saturated NaCl
  4. customdried
  5. concentrationconcentrated to a semi-solid
  6. customThe crude product is purified via column chromatography on silica gel (200 g)

Sources & evidence

ORD record
ord-c05e57aeb81c4ee2964fe72c0ac1ca47
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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