Isopropyl iodide → 4-bromo-1-isopropyl-1H-indole-3-carbaldehyde

HRID 402843Notes

Reaction equation

HRID 402843 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH:17]=[O:18])=[CH:11][NH:12]2.I[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[Br:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH:17]=[O:18])=[CH:11][N:12]2[CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 27631784-Bromo-1H-indole-3-carbaldehyde

Product 1

HCID 772308814-bromo-1-isopropyl-1H-indole-3-carbaldehydeYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (873 mg, 12.68 mmol) was added to a solution of 4-bromo-1H-indole-3-carboxaldehyde (200 mg, 0.893 mmol) in DMF (2.0 mL) and the mixture was stirred at room temperature for 10 minutes. Then 2-iodopropane (0.179 ml, 1.785 mmol) was added and the solution was stirred for 80° C. for 2 hours. The solution was cooled to room temperature and then partitioned between ethyl acetate and water and extracted twice with ethyl acetate. The organic layers were washed twice with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude title intermediate (175 mg).

Workup

  1. stirringthe solution was stirred for 80° C. for 2 hours
  2. temperatureThe solution was cooled to room temperature
  3. custompartitioned between ethyl acetate and water
  4. extractionextracted twice with ethyl acetate
  5. washThe organic layers were washed twice with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4b7a96204d941839e3a5e3697c4bfcc
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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