Methanol → 3-(pyridin-4-yl)-1-trityl-1H-indazol-5-amine

HRID 1465684Notes

Reaction equation

HRID 1465684 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[N:8]=[C:7]2[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1)([O-])=O.CO.[H][H]>C1(C)C=CC=CC=1.[Pd]>[N:35]1[CH:36]=[CH:37][C:32]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([NH2:1])[CH:5]=3)[N:9]([C:13]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]=2)=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 601460255-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 576858103-(pyridin-4-yl)-1-trityl-1H-indazol-5-amineYield 105.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

To a 500 ml round bottom flask equipped with a magnetic stir bar was added 5-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazole (1332 g, 27.6 mmol) and dissolved in a mixture of toluene:MeOH (120 ml: 40 ml). While stirring, Pd/C (1.5 g, 10% wet) was added. The mixture was then subjected to a hydrogen balloon and stirred overnight. Upon completion of the reaction, which was determined by LC/MS, the mixture was filtered through celite and concentrated under vacuum to give 3-(pyridin-4-yl)-1-trityl-1H-indazol-5-amine (13.21 g) as a yellow solid.

Workup

  1. customTo a 500 ml round bottom flask equipped with a magnetic stir bar
  2. stirringstirred overnight
  3. customUpon completion of the reaction, which
  4. filtrationthe mixture was filtered through celite
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9dd8083791dd43ca8fff325e53924604
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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