HCID 21249906, compound → 3-{2-[benzyl-(4-pyridin-3-yl-butyl)amino]ethyl}-2-(3,5-dimethylphenyl)-1H-indol-5-ylamine

HRID 1532372Notes

Reaction equation

HRID 1532372 reaction equation
[H][H].[CH2:3]([N:10]([CH2:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([N+:32]([O-])=O)[CH:30]=2)[NH:25][C:24]=1[C:35]1[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([CH3:42])[CH:36]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>[Ni]>[CH2:3]([N:10]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([NH2:32])[CH:30]=2)[NH:25][C:24]=1[C:35]1[CH:36]=[C:37]([CH3:42])[CH:38]=[C:39]([CH3:41])[CH:40]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 21249906HCID 21249906, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 212498943-{2-[benzyl-(4-pyridin-3-yl-butyl)amino]ethyl}-2-(3,5-dimethylphenyl)-1H-indol-5-ylamineYield 74.5%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a stirred solution of benzyl-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}-(4-pyridin-3-yl-butyl)amine (350 mg in 30 mL absolute ethanol) was added ca. 30 mg of Raney” nickel. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 3 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:4:1) gave the title compound (246 mg).

Workup

  1. customevacuated
  2. customAfter 3 hours the reaction was flushed with nitrogen
  3. filtrationfiltered over diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:4:1)

Sources & evidence

ORD record
ord-ebac83d33e4440d5b6cf6b9a579fd891
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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