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

HRID 589355Notes

Reaction equation

HRID 589355 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C>[CH2:1]([C:3]1[N:4]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:5]2[C:10]([C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 895902792-ethyl-3-(4-nitrobenzyl)-1H-indole

Product 1

HCID 89590281ethyl 2-[2-ethyl-3-(4-nitrobenzyl)-1H-indol-1-yl]acetateYield 8.97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Ethyl-3-(4-nitrobenzyl)-1H-indole (3.0 g, 10.7 mmol) was weighed, and dissolved in 30 mL DMF. Cesium carbonate (6.98 g, 21.4 mmol) was added, and stirred at room temperature for 15 min. Ethyl bromoacetate (1.97 g, 11.8 mmol) was added, reacted at room temperature for 10 h, and 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, purified by preparative liquid phase to obtain a yellow solid 350 mg, at a yield of 8.97%.

Workup

  1. customreacted at room temperature for 10 h
  2. filtrationfiltered
  3. additionThe filtrate was added into water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customa saturated solution of sodium chloride, rotate evaporated to dryness
  7. custompurified by preparative liquid phase

Sources & evidence

ORD record
ord-6a9e45f9b2804bae81ef43897a4fa8dd
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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