Iodoethane → Ethyl 6-cyano-1-ethylindole-2-carboxylate

HRID 1532338Notes

Reaction equation

HRID 1532338 reaction equation
[H-].[Na+].I[CH2:4][CH3:5].[C:6]([C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:14]2)=[CH:10][CH:9]=1)#[N:7]>CN(C)C=O.O>[C:6]([C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:14]2[CH2:4][CH3:5])=[CH:10][CH:9]=1)#[N:7]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 4715002Ethyl 6-cyano-1H-indole-2-carboxylate

Product 1

HCID 21251527Ethyl 6-cyano-1-ethylindole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 1 l flask, 23.5 g of ethyl 6-cyanoindole-2-carboxylate was dissolved in 300 ml of dimethylformamide, and 6.6 g of 60% NaH was slowly added thereto at 0° C. 17.6 ml of iodoethane was then added thereto at −10˜0° C. and the mixture was stirred for 2 hours at room temperature. The reaction solution was cooled and, after adding ice, diluted with water and then extracted three times with ethyl acetate. The organic extracts were combined, dried over MgSO4 and then evaporated. The residue was purified with silica gel column chromatography [eluent: ethyl acetate/n-hexane(1:3)]. The fractions containing the desired product were combined and then evaporated to obtain 26.2 g of the title compound as a yellow solid.

Workup

  1. customat 0° C
  2. temperatureThe reaction solution was cooled
  3. additionafter adding ice
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified with silica gel column chromatography [eluent: ethyl acetate/n-hexane(1:3)]
  8. additionThe fractions containing the desired product
  9. customevaporated

Sources & evidence

ORD record
ord-dc3e2711508f48df8b3988d06646cca6
Source dataset
uspto-grants-2001_03
Patent number
US06201006B1

Reaction notes

Loading…