Ethyl bromoacetate → HCID 86681634, compound

HRID 571219Notes

Reaction equation

HRID 571219 reaction equation
[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C>[N+:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 110841823-nitro-1H-indole

Product 1

HCID 86681634HCID 86681634, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-nitro-1H-indole (1 g, 6.17 mmol) in dry DMF (10 ml), under nitrogen, sodium hydride (60% w/w dispersion in mineral oil, 0.259 g, 6.48 mmol) was added. The mixture was stirred at room temperature for 15 minutes, and then ethyl 2-bromoacetate (0.723 ml, 6.17 mmol) was added. After stirring at the same temperature for 45 minutes, the mixture was partitioned between aqueous sat. NaHCO3 and Et2O; the aqueous layer was extracted with Et2O and the combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed and the resulting crude solid was purified by flash chromatography on silica gel (petroleum ether:Et2O from 6:4 to 1:1) to give ethyl 2-(3-nitro-1H-indol-1-yl)acetate (983 mg, 3.96 mmol, 64% yield). MS/ESI+ 249.1 [MH]+.

Workup

  1. stirringAfter stirring at the same temperature for 45 minutes
  2. customthe mixture was partitioned between aqueous sat. NaHCO3 and Et2O
  3. extractionthe aqueous layer was extracted with Et2O
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed
  7. customthe resulting crude solid was purified by flash chromatography on silica gel (petroleum ether:Et2O from 6:4 to 1:1)

Sources & evidence

ORD record
ord-aaa0100a1af942deaddd54fcef43e341
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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