Potassium Carbonate → HCID 67086835, compound

HRID 2365571Notes

Reaction equation

HRID 2365571 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.Cl[CH2:15][C:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH3:13][O:12][C:10]([C:5]1[C:4]2[CH:3]=[CH:2][N:1]([CH2:15][C:16](=[O:17])[N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 67086835HCID 67086835, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl indole-4-carboxylate (50 mg, 2.85 mmol) and 2-chloro-N,N-diethylacetamide (854 mg, 5.71 mmol) are dissolved in DMF (10 ml) and to the solution is added potassium carbonate (986 mg, 7.14 mmol). The reaction is heated using microwave radiation at 100° C. for 2 hours, then diluted with DCM (60 ml) and washed with water (5×10 ml). Drying over MgSO4, concentration in vacuo, and trituration with Et2O affords 1-Diethylcarbamoylmethyl-1H-indole-4-carboxylic acid methyl ester; [M+H]+ 289.

Workup

  1. temperatureThe reaction is heated
  2. customat 100° C.
  3. customfor 2 hours
  4. washwashed with water (5×10 ml)
  5. dry with materialDrying over MgSO4, concentration in vacuo, and trituration with Et2O

Sources & evidence

ORD record
ord-8de042ea7d2c43e7b765b260320be829
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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