Ethyl bromoacetate → HCID 14636514, compound

HRID 1166731Notes

Reaction equation

HRID 1166731 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=[O:2].[H-].[Na+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C>[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 14636514HCID 14636514, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
15 °C

Procedure

3-Formylindole (10.0 g, 69 mmoles) was dissolved in DMF (100 ml). Under N2 was a 60% suspension of NaH in mineral oil (3.0 g) added in portions with cooling (temp<15° C.). At <15° C. was a solution of ethyl bromoacetate (8.4 ml) in DMF (15 ml) added drop wise over 30 minutes. The resulting mixture was stirred at room temperature for 16 hours and evaporated in vacuo. The residue was added water (300 ml) and extracted with ethyl acetate (2×150 ml), the combined organic extracts were washed with satd. NH4Cl, dried (MgSO4) and concentrated to afford 15.9 g ethyl (3-formylindolyl)acetate.

Workup

  1. additionadded in portions
  2. customAt <15° C.
  3. additionadded drop wise over 30 minutes
  4. customevaporated in vacuo
  5. additionThe residue was added water (300 ml)
  6. extractionextracted with ethyl acetate (2×150 ml)
  7. washthe combined organic extracts were washed with satd
  8. dry with materialNH4Cl, dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-435aad256e32418abc8330c9450271da
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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