1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline → 1-(2-(Indolin-1-yl)ethyl)-1H-pyrazol-4-amine

HRID 624037Notes

Reaction equation

HRID 624037 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)[CH:8]=1)([O-])=O>CCOC(C)=O.CCO.O=[Pt]=O>[N:11]1([CH2:10][CH2:9][N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 1

HCID 682835761-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline

Product 1

HCID 621388071-(2-(Indolin-1-yl)ethyl)-1H-pyrazol-4-amine

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline (183 mg, 0.71 mmol) in EtOAc (0.7 mL, degassed) and EtOH (2 mL, degassed), PtO2 (14 mg, 0.07 mmol) was added and the reaction mixture was stirred at rt under a H2-atmosphere for 18 h. The mixture was diluted with EtOH, filtered over celite and the filter cake was rinsed with EtOH. The filtrate was concentrated to obtain the title compound as an oil, which was used in the next step without further purification. LC-MS conditions A: tR=0.51 min, [M+H]+=229.26.

Workup

  1. filtrationfiltered over celite
  2. washthe filter cake was rinsed with EtOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9580a8ee934d42178a693706bf38d015
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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