5-methoxy-3-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)-1H-indole → 1-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-1H-pyrazol-4-ylamine

HRID 624046Notes

Reaction equation

HRID 624046 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[N:15]1>[Pd].CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[CH:18]=[C:17]([NH2:19])[CH:16]=[N:15]1

Participants

4

Reactant 1

HCID 867042135-methoxy-3-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)-1H-indole

Product 1

HCID 682831151-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-1H-pyrazol-4-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a round bottom flask 5-methoxy-3-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)-1H-indole (2.11 g, 7.37 mmol), Pd/C (200 mg) and EtOH (35 mL, degassed) was added. The flask was evacuated and backfilled with H2 and the reaction mixture was stirred under H2-atmosphere at rt for 18 h. The reaction mixture was filtered over celite, washed with EtOH and the solvent was removed under reduced pressure to yield the title compound as a red oil, which was used in the next step without further purification. LC-MS conditions B: tR=0.42 min, [M+H]+=257.16.

Workup

  1. customThe flask was evacuated
  2. filtrationThe reaction mixture was filtered over celite
  3. washwashed with EtOH
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-15ad271e3bff43fbbb6847f11ad9c8b4
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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