Iodoethane → 1-ethyl-6-methoxy-2-methyl-1H-indole-3-carbonitrile

HRID 252514Notes

Reaction equation

HRID 252514 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:15]#[N:16])=[C:10]([CH3:14])[NH:11]2)=[CH:7][CH:6]=1.[CH2:17](I)[CH3:18]>CN(C=O)C>[CH2:17]([N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([O:4][CH3:3])[CH:13]=2)[C:9]([C:15]#[N:16])=[C:10]1[CH3:14])[CH3:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 139046406-methoxy-2-methyl-1H-indole-3-carbonitrile

Product 1

HCID 594252651-ethyl-6-methoxy-2-methyl-1H-indole-3-carbonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (0.6 g, 2 eq.) in DMF (7 mL) is added a solution of 6-methoxy-2-methyl-1H-indole-3-carbonitrile (1.3 g, 7.0 mmol) in DMF (8 mL) followed by ethyl iodide (1.2 mL, 2 eq.) at 0° C. After stirring for 1 h, the mixture is poured into ice water and then extracted with CH2Cl2. The organic layer is washed with brine and dried with Na2SO4. The solvent is evaporated under vacuum and purified with flash column chromatography on silica gel using EtOAc/petroleum ether (1/5) as eluent to yield 92% of 1-ethyl-6-methoxy-2-methyl-1H-indole-3-carbonitrile.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer is washed with brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent is evaporated under vacuum
  5. custompurified with flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ff3633a85fb14e399d26b5a8775f5ede
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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