Benzyl Bromide → HCID 18355353, compound

HRID 429648Notes

Reaction equation

HRID 429648 reaction equation
[CH:1]([C:3]1[C:11]2[C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][CH:4]=1)=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O.C(OCC)(=O)C.O>[CH:1]([C:3]1[C:11]2[C:10]([C:12]([O:14][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][CH:4]=1)=[O:2]

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 219013933-Formyl-1H-indole-4-carboxylic acid

Product 1

HCID 18355353HCID 18355353, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-formylindole-4-carboxylic acid (390 mg) and potassium carbonate (285 mg) in N,N-dimethylformamide (10 ml) was added benzyl bromide (353 mg) at ambient temperature and the mixture was stirred for 4 hours. The resulting mixture was diluted with ethyl acetate and water, then the layers were separated. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residual solid was triturated with diethyl ether:n-hexane (1:6) to give benzyl 3-formylindole-4-carboxylate (520 mg).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residual solid was triturated with diethyl ether:n-hexane (1:6)

Sources & evidence

ORD record
ord-3dd551704da64c66bc87e665d4356671
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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