Iodoethane → 1-Ethyl-6-trifluoromethoxyindole-3-carbonitrile

HRID 506107Notes

Reaction equation

HRID 506107 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.ClS([N:19]=[C:20]=O)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH2:28](I)[CH3:29]>CN(C=O)C>[CH2:28]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([O:3][C:2]([F:1])([F:13])[F:14])[CH:12]=2)[C:8]([C:20]#[N:19])=[CH:9]1)[CH3:29]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 70918Chlorosulfonyl isocyanateHCID 220489586-(Trifluoromethoxy)-1H-indole

Product 1

HCID 594258351-Ethyl-6-trifluoromethoxyindole-3-carbonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-trifluoromethoxyindole (2.68 g, 13.3 mmol) in dry DMF (10 mL) at 0° C., is added chlorosulfonylisocyanate (2.35 g, 1.44 mL, 16.6 mmol). The mixture is then brought to room temperature slowly and stirred for 1 h. The mixture is poured into ice (100 mL) and stirred for 1 h. The precipitate is collected by filtration and washed thoroughly with water and dried in vacuo, which is then dissolved in DMF (15 mL). To the solution is added K2CO3 and EtI (2.59 g, 1.34 mL, 16.6 mmol), and the mixture is stirred at 50° C. overnight. It is then poured into ice-water (200 mL). The precipitate is collected by filtration and washed with water, dried in air and purified by chromatography (silica gel, DCM) to furnish 1-ethyl-6-trifluoromethoxyindole-3-carbonitrile (2.90 g, 86%).

Workup

  1. customis then brought to room temperature
  2. stirringstirred for 1 h
  3. filtrationThe precipitate is collected by filtration
  4. washwashed thoroughly with water
  5. customdried in vacuo, which
  6. dissolutionis then dissolved in DMF (15 mL)
  7. stirringthe mixture is stirred at 50° C. overnight
  8. filtrationThe precipitate is collected by filtration
  9. washwashed with water
  10. customdried in air
  11. custompurified by chromatography (silica gel, DCM)

Sources & evidence

ORD record
ord-57889372f990460cb4e04f91ccbcdc83
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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