Water → Methyl 1-benzylindole-3-carboxylate

HRID 1372695Notes

Reaction equation

HRID 1372695 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[CH2:16]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 952042Methyl 1-benzylindole-3-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% in oil, 274.1 mg, 6.853 mmol) was suspended in DMF (8.0 ml). To the resulting suspension was added methyl indole-3-carboxylate (400.2 mg, 2.284 mmol) under stirring at 0° C., followed by stirring at the same temperature for 30 minutes. To the reaction mixture was added benzyl bromide (0.41 ml, 3.427 mmol) at 0° C. After stirring at room temperature for 1 hour, the reaction mixture was added with water to terminate the reaction. The reaction mixture was then extracted with ethyl acetate. The extract was washed with 1N HCl, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (6:1, v/v) eluate fractions, methyl 1-benzylindole-3-carboxylate (100%) was obtained as a gum.

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. stirringAfter stirring at room temperature for 1 hour
  3. customto terminate
  4. customthe reaction
  5. extractionThe reaction mixture was then extracted with ethyl acetate
  6. washThe extract was washed with 1N HCl
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (6:1

Sources & evidence

ORD record
ord-b69d27407e3a4376a7ff4abfcc70a09b
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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