5-methoxy-1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline → 1-[3-(5-Methoxy-2,3-dihydro-indol-1-yl)-propyl]-1H-pyrazol-4-ylamine

HRID 624040Notes

Reaction equation

HRID 624040 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[N:16]1)[CH2:7][CH2:6]2>CO.O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([NH2:20])[CH:17]=[N:16]1)[CH2:7][CH2:6]2

Participants

4

Reactant 1

HCID 682831945-methoxy-1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline

Product 1

HCID 682827831-[3-(5-Methoxy-2,3-dihydro-indol-1-yl)-propyl]-1H-pyrazol-4-ylamine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 5-methoxy-1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline (1.18 mmol), in MeOH (6.0 mL, degassed), PtO2 (12 mg, 0.05 mmol) was added and the reaction mixture was stirred at rt under a H2-atmosphere for 18 h. The mixture was diluted with MeOH, filtered over celite and the filter cake was rinsed with MeOH. The filtrate was concentrated to obtain the title compound as a brown oil, which was used in the next step without further purification. LC-MS conditions B: tR=0.32 min, [M+H]+=273.1.

Workup

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

Sources & evidence

ORD record
ord-229fd97de6c8476a8f3ce7215fe67cf1
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

Loading…