Potassium Carbonate → HCID 86707250, compound

HRID 878980Notes

Reaction equation

HRID 878980 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21]Cl>CN(C)C=O>[CH3:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 27734351H-Indole-6-carboxaldehyde

Product 1

HCID 86707250HCID 86707250, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of indole-6-carboxaldehyde (457 mg) in N,N-dimethylformamide (5 mL) were added potassium carbonate (936 mg) and 2,6-dimethylbenzyl chloride (752 mg) at room temperature, and then the reaction mixture was subjected to microwave irradiation at 160° C. for 30 minutes. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (740 mg) as a yellow solid.

Workup

  1. customirradiation at 160° C. for 30 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9213c032f6a4439a8c1a64aede33570e
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

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