1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline → 1-[3-(2,3-Dihydro-indol-1-yl)-propyl]-1H-pyrazol-4-ylamine

HRID 624023Notes

Reaction equation

HRID 624023 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][CH2:11][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH:8]=1)([O-])=O>[Pd].CO>[N:12]1([CH2:11][CH2:10][CH2:9][N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 867042081-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline

Product 1

HCID 682827791-[3-(2,3-Dihydro-indol-1-yl)-propyl]-1H-pyrazol-4-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a round bottom flask was added 1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline (2.10 g, 7.70 mmol), Pd/C (210 mg) and MeOH (48 mL, degassed). 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 MeOH and the solvent was removed under reduced pressure to yield the title compound as a red oil. LC-MS conditions

Workup

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

Sources & evidence

ORD record
ord-ed6c4acc10cd46c1b28db97edcb830d6
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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