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

HRID 506021Notes

Reaction equation

HRID 506021 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-c972adf366224ac1964d1f2fb3305c0d
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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