Ethyl bromoacetate → HCID 69054050, compound

HRID 490681Notes

Reaction equation

HRID 490681 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:11][CH3:12])=[CH:6][CH:5]=2.[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:3]1[C:4]2[C:9](=[CH:8][C:7]([O:11][CH3:12])=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1])[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 706425-Methoxy-2-methylindole

Product 1

HCID 69054050HCID 69054050, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-5-methoxylindole (5.10 g, 31.6 mmol) in DMF (200 mL) is added sodium hydride (60%, 1.9 g, 47.4 mmol) at 0˜5° C., stirred for 30 min, ethyl 2-bromoacetate (8.35 g, 50 mmol) is added. After 2 hr at room temperature, the reaction is quenched by water, extracted with ether. Combined organic layers are washed with water and brine, dried over sodium sulfate. Concentration yields the crude title product, which is used for next step without further purification.

Workup

  1. waitAfter 2 hr at room temperature
  2. customthe reaction is quenched by water
  3. extractionextracted with ether
  4. washCombined organic layers are washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration

Sources & evidence

ORD record
ord-352a4be9584944b1b34e4438f809e0e5
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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