2-tert-butyl-3-(2,2-dimethoxy-ethyl)-6-nitro-1H-indole → 2-tert-butyl-3-(2,2-dimethoxy-ethyl)-1H-indol-6-ylamine

HRID 1802760Notes

Reaction equation

HRID 1802760 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:14][CH:15]([O:18][CH3:19])[O:16][CH3:17])=[CH:11][CH:10]=[C:9]([N+:20]([O-])=O)[CH:8]=2)([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:14][CH:15]([O:16][CH3:17])[O:18][CH3:19])=[CH:11][CH:10]=[C:9]([NH2:20])[CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 578992342-tert-butyl-3-(2,2-dimethoxy-ethyl)-6-nitro-1H-indole

Product 1

HCID 578993052-tert-butyl-3-(2,2-dimethoxy-ethyl)-1H-indol-6-ylamineYield 63%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl-3-(2,2-dimethoxy-ethyl)-6-nitro-1H-indole (611 mg, 2 mmol) in methanol was added palladium hydroxide on carbon (100 mg). The flask was evacuated and purged with hydrogen gas three times. The reaction was stirred under hydrogen for 16 h and filtered through a pad of Celite, which was rinsed with methanol. The organic solution was combined and concentrated in vacuo and the residue was purified via flash chromatography to give the desired product (347 mg, 63% yield).

Workup

  1. customThe flask was evacuated
  2. custompurged with hydrogen gas three times
  3. filtrationfiltered through a pad of Celite, which
  4. washwas rinsed with methanol
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-02ad594c6d7a46cb93bdc5b1a6e839d4
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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