6-(1H-Indol-4-yl)-1-methyl-4-nitro-1H-indazole → 6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-amine

HRID 1615978Notes

Reaction equation

HRID 1615978 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][N:16]4[CH3:19])=[C:12]([N+:20]([O-])=O)[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1>C(OCC)(=O)C.[Pd]>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([NH2:20])[C:13]4[CH:14]=[N:15][N:16]([CH3:19])[C:17]=4[CH:18]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 582679906-(1H-Indol-4-yl)-1-methyl-4-nitro-1H-indazole

Product 1

HCID 582680236-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-amineYield 157%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-(1H-Indol-4-yl)-1-methyl-4-nitro-1H-indazole (49 mg, 0.17 mmol) was dissolved in ethyl acetate (10 ml) and treated with 10% Pd/C (5 mg) then stirred under hydrogen for 2 h before stirring under nitrogen over the weekend. The reaction was filtered through a Celite cartridge, washing with ethyl acetate, then evaporated to dryness to give the title compound (70 mg) as a grey solid.

Workup

  1. stirringbefore stirring under nitrogen over the weekend
  2. filtrationThe reaction was filtered through a Celite cartridge
  3. washwashing with ethyl acetate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a1d29d93a55e4fcc90747150e8e20905
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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