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

HRID 589356Notes

Reaction equation

HRID 589356 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:5]2[C:10]([C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:2]>CO.[Pd]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:3]=2[CH2:1][CH3:2])=[CH:18][CH:17]=1

Participants

4

Reactant 1

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

Product 1

HCID 89590280ethyl 2-[3-(4-aminobenzyl)-2-ethyl-1H-indol-1-yl]acetateYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a dry reaction vessel, ethyl 2-[2-ethyl-3-(4-nitrobenzyl)-1H-indol-1-yl]acetate (350 mg, 0.96 mmol) was added, and dissolved in 10 mL methanol. 10% Pd/C 50 mg was added, purged with dry hydrogen, and reacted for 1 h. After completion of the reaction, it was filtered, and the filter cake was washed with methanol. The filtrate was rotate evaporated to dryness to obtain a white solid 288 mg, at a yield of 89.6%.

Workup

  1. additionwas added
  2. custompurged with dry hydrogen
  3. customreacted for 1 h
  4. customAfter completion of the reaction, it
  5. filtrationwas filtered
  6. washthe filter cake was washed with methanol
  7. customThe filtrate was rotate evaporated to dryness

Sources & evidence

ORD record
ord-25c061abf3814faa822591931b67c805
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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