Benzyl Bromide → 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde

HRID 16628

Reaction equation

HRID 16628 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.CCOC(C)=O>[CH2:22]([N:3]1[C:4]2[C:9](=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2)[C:10]([CH:11]=[O:12])=[C:2]1[CH3:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 6093592-methyl-5-nitro-1H-indole-3-carbaldehyde

Product 1

HCID 28382531-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehydeYield 83.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-5-nitro-1H-indole-3-carboxaldehyde (500 mg, 2.45 mmol) in DMF (5 ml) was added potassium carbonate (1.0 g, 7.35 mmol) and benzyl bromide (0.44 ml, 3.68 mmol). The mixture was stirred at room temperature for 4 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was triturated with Et2O-hexane to yield 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde (Compound 50) as a yellow solid (600 mg, 83%).

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with Et2O-hexane

Sources & evidence

ORD record
ord-02e4b9ab0bf74da998fa4be994fe94f7
Source dataset
uspto-grants-2010_06
Patent number
US07737173B2

Linked notes

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