1-(2-(5,6-dimethoxyindolin-1-yl)ethyl)-1H-pyrazol-4-amine → 1-[2-(5,6-Dimethoxy-indol-1-yl)-ethyl]-1H-pyrazol-4-ylamine

HRID 624019Notes

Reaction equation

HRID 624019 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]([NH2:21])[CH:18]=[N:17]1)[CH2:7][CH2:6]2>CC(C)=O.O=[Mn]=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)[CH:7]=[CH:6]2

Participants

4

Reactant 1

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

Product 1

HCID 682827821-[2-(5,6-Dimethoxy-indol-1-yl)-ethyl]-1H-pyrazol-4-ylamine

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent2×

Procedure

A solution of 1-(2-(5,6-dimethoxyindolin-1-yl)ethyl)-1H-pyrazol-4-amine (1.36 g, 4.70 mmol) in acetone (10 mL) was added dropwise to a suspension of MnO2 (817 mg, 9.41 mmol) in aceton (10 mL). The resulting dark reaction mixture was stirred at rt overnight, then filtered over celite, washed with acetone and the filtrate was concentrated under reduced pressure. Purification was performed by FC (DCM/MeOH 98:2→95:5) to yield the title compound as a brown oil. LC-MS conditions B: tR=0.41 min, [M+H]+=287.18.

Workup

  1. customThe resulting dark reaction mixture
  2. filtrationfiltered over celite
  3. washwashed with acetone
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-f9add7a71c294a1c864bf4085d8aae89
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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