1-tert-butyl 2-ethyl 5-(2-methoxyethoxy)-7-nitro-1H-indole-1,2-dicarboxylate → HCID 59303538, compound

HRID 504820Notes

Reaction equation

HRID 504820 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([N+:15]([O-])=O)[CH:14]=1)[N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:10]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:9]2>[C].[Pd].O1CCCC1>[NH2:15][C:13]1[CH:14]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=[C:8]2[C:12]=1[N:11]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH:10]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:9]2

Participants

4

Reactant 1

HCID 575032131-tert-butyl 2-ethyl 5-(2-methoxyethoxy)-7-nitro-1H-indole-1,2-dicarboxylate

Product 1

HCID 59303538HCID 59303538, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-tert-butyl 2-ethyl 5-(2-methoxyethoxy)-7-nitro-1H-indole-1,2-dicarboxylate (3.9 g), 10% palladium-carbon (50% containing water, 400 mg) and tetrahydrofuran (80 mL) was stirred at room temperature under hydrogen atmosphere at normal pressure for 6 hr. The catalyst was filtered off, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give the title compound (3.22 g, yield 89%) as a colorless solid from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e7e2c65ceeda4b1a89865c173af5a92a
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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