Water → HCID 17221165, compound

HRID 508581Notes

Reaction equation

HRID 508581 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.O>CN(C=O)C>[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:1]2[C:9]3[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 680214-Fluorobenzyl bromideHCID 589040Indole-5-carboxaldehyde

Product 1

HCID 17221165HCID 17221165, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Indole-5-carboaldehyde (1.0 g) was dissolved in DMF (14 mL), and potassium hydroxide (460 mg) and 4-fluorobenzyl bromide (1.4 g) were sequentially added thereto under ice cooling. The mixture was stirred for 65 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (20% to 50% ethyl acetate/hexane), and the title compound (1.2 g) was obtained as a pale yellow solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (20% to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-71e82b854291411994503fec34389ea0
Source dataset
uspto-grants-2015_08
Patent number
US09096531B2

Reaction notes

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