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

HRID 907121Notes

Reaction equation

HRID 907121 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) was 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 was poured into ice water and the extracted with CH2Cl2. The organic layer was washed with brine and dried with Na2SO4. The solvent was 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. extractionthe extracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent was evaporated under vacuum
  5. custompurified with flash column chromatography on silica gel

Sources & evidence

ORD record
ord-bdfe014327f743f0ba8b0e9e6530ca33
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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