Ethyl bromoacetate → Ethyl 2-(6-nitro-1H-indol-1-yl)acetate

HRID 453865Notes

Reaction equation

HRID 453865 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C>[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][N:12]2[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 785026-Nitro-1H-indole

Product 1

HCID 43308826Ethyl 2-(6-nitro-1H-indol-1-yl)acetateYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (37 mmol, 2 equiv.) was taken up in DMF (25 ml) and cooled to 0° C. 6-Nitro-1H-indole (18.5 mmol, 1 equiv.) was added in portions, and the mixture was stirred for 1 h at 25° C. The reaction mixture was cooled to 0° C. again, ethyl bromoacetate (22.22 mmol, 1.2 equiv.) was added dropwise, and the mixture was stirred for 2 h at 25° C. The reaction mixture was then poured into ice-water and extracted with ethyl acetate (2×100 ml). The combined organic phases were washed with sat. NaCl solution (30 ml), dried over Na2SO4 and concentrated under reduced pressure. The product was crystallized from hexane and was used in the next step without being purified further. Yield: 57%

Workup

  1. temperatureThe reaction mixture was cooled to 0° C. again
  2. stirringthe mixture was stirred for 2 h at 25° C
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. washThe combined organic phases were washed with sat. NaCl solution (30 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe product was crystallized from hexane
  8. customwithout being purified further

Sources & evidence

ORD record
ord-a9a05c66925648a1b5316372cb08aa8e
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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