1H-indole-6-carbonitrile → HCID 15490886, compound

HRID 1978822Notes

Reaction equation

HRID 1978822 reaction equation
CC([O-])(C)C.[K+].[C:7]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1)#[N:8].CC1C=CC=CC=1S(O[CH2:29][CH:30]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31]1)(=O)=O>O1CCCC1>[C:7]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:29][CH:30]2[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36])[CH2:31]2)=[CH:11][CH:10]=1)#[N:8]

Participants

5

Reactant 3

HCID 851461H-indole-6-carbonitrileHCID 21201384HCID 21201384, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15490886HCID 15490886, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

77 mmol of potassium tert-butylate are added to a solution of 70 mmol of 6-cyanoindole in 400 ml of tetrahydrofuran. After 10 minutes' stirring at room temperature, 70 mmol of tert-butyl 3-[(methylphenyl)sulphonyloxymethyl]-1-pyrrolidinecarboxylate in 60 ml of tetrahydrofuran are added. The reaction mixture is heated at reflux for 12 hours. After cooling and dilution with water, the solvent is removed by evaporation. The residue is extracted with dichloromethane and the organic phase is washed with water, dried and concentrated to yield the expected product.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 12 hours
  3. temperatureAfter cooling
  4. customdilution with water, the solvent is removed by evaporation
  5. extractionThe residue is extracted with dichloromethane
  6. washthe organic phase is washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d858b49666934ec78072c080364123e0
Source dataset
uspto-grants-2001_05
Patent number
US06239129B1

Reaction notes

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