Benzyl Bromide → 1-benzyl-1H-indole-3-carbaldehyde

HRID 1854663Notes

Reaction equation

HRID 1854663 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CS(C)=O.C(OCC)(=O)C.[NH4+].[Cl-]>[CH2:14]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 2621041-benzyl-1H-indole-3-carbaldehydeYield 31%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 1H-indole-3-carboxaldehyde (300 mg, 2.07 mmol) in 4.1 mL of dry dimethylsulfoxide was added sodium hydride (108 mg, 55%, 2.5 mmol) under nitrogen at 0° C. After the reaction mixture was stirred at room temperature for 30 min, benzyl bromide (0.40 mL, 2.5 mmol) was added with additional stirring for 2 h. The reaction mixture was diluted with 10 mL of ethyl acetate and 10 mL of saturated NH4Cl aqueous solution at 0° C., successively, and extracted with 100 mL of ethyl acetate. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 70/30) to obtain the title compound as a pale brown solid (10.8 mg, 31%).

Workup

  1. stirringwith additional stirring for 2 h
  2. extractionsuccessively, and extracted with 100 mL of ethyl acetate
  3. washThe extract was washed with saturated NaHCO3 aqueous solution, brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 70/30)

Sources & evidence

ORD record
ord-8342edf50a7c469a95f777be823fbf97
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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