Diethylcarbamoyl chloride → 5-Bromo-3-formyl-indole-1-carboxylic acid diethylamide

HRID 1454771Notes

Reaction equation

HRID 1454771 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]=[O:14].[CH2:15]([N:17]([CH2:21][CH3:22])[C:18](Cl)=[O:19])[CH3:16]>C1COCC1>[CH2:15]([N:17]([CH2:21][CH3:22])[C:18]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([Br:3])=[CH:12][CH:11]=2)[C:7]([CH:13]=[O:14])=[CH:8]1)=[O:19])[CH3:16]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 24758Sodium hydrideHCID 701375-Bromoindole-3-carbaldehyde

Product 1

HCID 860263405-Bromo-3-formyl-indole-1-carboxylic acid diethylamideYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (0.93 g, 37 mmol) in anhydrous THF (75 mL) was added dropwise a solution of 5-bromo-1H-indole-3-carbaldehyde (7.5 g, 34 mmol) in anhydrous THF (60 ml) at 0° C. After stirring at 0° C. for 15 min, N,N-diethylcarbamyl chloride (5.0 g, 37 mmol) was added dropwise into the reaction mixture. The mixture was warmed to room temperature and stirred overnight. The reaction was then quenched with water and extracted with ethyl acetate. The organics were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was crystallized from ether/hexane to give the title compound (8.75 g, 80%) as a white solid.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred overnight
  3. customThe reaction was then quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organics were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-84dbad115b654a73b6c4025f76423366
Source dataset
uspto-grants-2009_01
Patent number
US07482330B2

Reaction notes

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