Water → HCID 43152078, compound

HRID 571190Notes

Reaction equation

HRID 571190 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[H-].[Na+].Br[CH2:15][C:16]([O:18][CH3:19])=[O:17].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 138725-MethoxyindoleHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 43152078HCID 43152078, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-methoxy-1H-indole (500 mg, 3.40 mmol) in dry DMF (8 ml), cooled at 0° C., sodium hydride (60% w/w dispersion in mineral oil, 136 mg, 3.40 mmol) was slowly added portionwise and the reaction was stirred at 0° C. for 45 minutes; then methyl 2-bromoacetate (315 μl, 3.40 mmol) was added dropwise, and the reaction was stirred at room temperature for 15 hours. Water was slowly added, and the product was extracted with Et2O and then with ethyl acetate. The combined organic layers were washed with water, dried over Na2SO4 and evaporated to dryness. The title compound was obtained and used for the next step without further purification (745 mg, 3.40 mmol, quantitative yield). MS/ESI+ 220.1 [MH]+.

Workup

  1. stirringthe reaction was stirred at room temperature for 15 hours
  2. extractionthe product was extracted with Et2O
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-25b2922d4fa8455e9b1dffbdbf33088f
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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