Potassium Carbonate → HCID 10316915, compound

HRID 743166Notes

Reaction equation

HRID 743166 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]=1[S:20][CH3:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.Cl.[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27]Cl.C([O-])([O-])=O.[K+].[K+]>CCO>[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([C:9]([NH:8][C:1]2[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:10])=[C:12]1[S:20][CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 14943553HCID 14943553, compound

Product 1

HCID 10316915HCID 10316915, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(methylthio)-N-phenyl-1H-indole-3-carboxamide [XXV: R8 =H] (1.8 g, 6.4 mmol) in EtOH (400 mL) was treated with 3-(dimethylamino)propyl chloride hydrochloride (10.0 g, 64 mmol) and K2CO3 (13 g, 96 mmol ) and heated under reflux for 3 hours. A further 10 equivalents of the reagents were then added, and the mixture was heated under reflux for a further 48 hours. EtOH was removed under reduced pressure, and the residue was diluted with water to give crude product. This was chromatographed on alumina, eluting with CH2Cl2 containing 0.2% MeOH, to give 1-[3-(dimethylamino)propyl]-2-(methylthio)-N-phenyl-1H-indole-3-carboxamide [XXVI: R8 =H, R9 =(CH2)3NMe2 ] (0.49 g, 21%) as an oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 48 hours
  5. customEtOH was removed under reduced pressure
  6. additionthe residue was diluted with water
  7. customto give crude product
  8. customThis was chromatographed on alumina
  9. washeluting with CH2Cl2 containing 0.2% MeOH

Sources & evidence

ORD record
ord-39b18d465c8c4087a79ebfa481b200e8
Source dataset
uspto-grants-1996_09
Patent number
US05556874

Reaction notes

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