Ethyl bromoacetate → ethyl 2-[2-methyl-3-(4-nitrobenzyl)-1H-indol-1-yl]acetate

HRID 589337Notes

Reaction equation

HRID 589337 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN(C=O)C>[CH3:1][C:2]1[N:3]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 861743212-Methyl-3-(4-nitrobenzyl)-1H-indole

Product 1

HCID 89590291ethyl 2-[2-methyl-3-(4-nitrobenzyl)-1H-indol-1-yl]acetateYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methyl-3-(4-nitrobenzyl)-1H-indole (4.0 g, 15 mmol) was weighed, and dissolved in 30 mL DMF. Cesium carbonate (9.77 g, 30 mmol) was added, and stirred at room temperature for 15 min. Ethyl bromoacetate (2.755 g, 16.5 mmol) was added, and reacted at room temperature for 3 h. Upon completion of the reaction, it was filtered. The filtrate was added into water, and extracted with ethyl acetate. The extract was washed with water, and a saturated solution of sodium chloride, rotate evaporated to dryness, chromatographed on a silica gel column (petroleum ether) to obtain a yellow solid 2.7 g, at a yield of 51.1%.

Workup

  1. customreacted at room temperature for 3 h
  2. customUpon completion of the reaction, it
  3. filtrationwas filtered
  4. additionThe filtrate was added into water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customa saturated solution of sodium chloride, rotate evaporated to dryness
  8. customchromatographed on a silica gel column (petroleum ether)

Sources & evidence

ORD record
ord-c1dc816cd50849cb856c80d5e35c4f0e
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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