5,6-dimethoxy-1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline → 1-(2-(5,6-dimethoxyindolin-1-yl)ethyl)-1H-pyrazol-4-amine

HRID 624018Notes

Reaction equation

HRID 624018 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][CH2:15][N:16]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[N:17]1)[CH2:7][CH2:6]2>CO.CCO.O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][CH2:15][N:16]1[CH:20]=[C:19]([NH2:21])[CH:18]=[N:17]1)[CH2:7][CH2:6]2

Participants

5

Reactant 1

HCID 682834525,6-dimethoxy-1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline

Product 1

HCID 682827781-(2-(5,6-dimethoxyindolin-1-yl)ethyl)-1H-pyrazol-4-amine

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 5,6-dimethoxy-1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline (1.53 g, 4.81 mmol) in MeOH (50 mL), PtO2 (200 mg, 0.88 mmol) was added and the reaction mixture was stirred at rt under a H2-atmosphere for 1 h. The mixture was diluted with EtOH, filtered over celite and the filter cake was rinsed with MeOH. The filtrate was concentrated under reduced pressure to obtain 1-(2-(5,6-dimethoxyindolin-1-yl)ethyl)-1H-pyrazol-4-amine as a brown oil, which was used in the next step without further purification. LC-MS conditions B: tR=0.38 min, [M+H]+=289.18.

Workup

  1. filtrationfiltered over celite
  2. washthe filter cake was rinsed with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2f49e3290d7e4904989bf2634b316758
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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