Dimethylformamide → 5-(tert-Butyl)-1H-indole-3-carbonitrile

HRID 1604627Notes

Reaction equation

HRID 1604627 reaction equation
ClS([N:5]=[C:6]=O)(=O)=O.[C:8]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2)([CH3:11])([CH3:10])[CH3:9].CN(C)C=O>C(#N)C>[C:8]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[C:6]#[N:5])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 219400865-(tert-Butyl)-1H-indole

Product 1

HCID 196036965-(tert-Butyl)-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Chlorosulfonyl isocyanate (1 ml) was added dropwise to a suspension of 5-tert-butylindole (2.1 g) in acetonitrile (15 ml) over 10 minutes under ice-cooling. After being stirred for 1 hour at same temperature, a solution of N,N-dimethylformamide (1 ml) in acetonitrile (20 ml) was added to the mixture and then the mixture was stirred at 50° C. for 1 hour. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and n-hexane. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 5-tert-butyl-3-cyanoindole (1.20 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 50° C. for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. washeluted with a mixture of ethyl acetate and n-hexane
  8. additionThe fractions containing the objective compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-614353461e004c69b9f023d9c568d939
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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