3-Methyl-1-(4-methylbenzene-1-sulfonyl)-6-nitro-1H-indazole → 3-methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-ylamine

HRID 1691805Notes

Reaction equation

HRID 1691805 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[N:4]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[N:3]=1.[H][H]>CO.[Pd]>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[N:4]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[N:3]=1

Participants

5

Reactant 2

HCID 123206643-Methyl-1-(4-methylbenzene-1-sulfonyl)-6-nitro-1H-indazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 593777823-methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-ylamineYield 38.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Methyl-6-nitro-1-(toluene-4-sulfonyl)-1H-indazole (750 mg, 2.26 mmol) was dissolved in 30 ml of methanol at room temperature. 10% Palladium on Carbon (200 mg) was added and the mixture was stirred under a balloon of hydrogen overnight. The mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (gradient 9:1 to 4:1 Hexanes/Ethyl Acetate) to give 3-methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-ylamine (265 mg, 38.9%) as a light tan crystalline solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography (gradient 9:1 to 4:1 Hexanes/Ethyl Acetate)

Sources & evidence

ORD record
ord-8902edcb74ea4ccdb69032fe15de16b2
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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