HCID 69036629, compound → HCID 55270289, compound

HRID 1930373Notes

Reaction equation

HRID 1930373 reaction equation
[C:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([N+:14]([O-])=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([NH2:14])=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69036629HCID 69036629, compound

Product 1

HCID 55270289HCID 55270289, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-tert-butyl-3-nitro-1 H-indazole (3.0 g, 14 mmol) and Pd/C (1 g) in MeOH (50 mL) was hydrogenated (1 atm) at RT for 2 h. The reaction mixture was filtered and the filtrate was concentrated and purified by chromatography to give 1-tert-butyl-1 H-indazol-3-ylamine (1.7 g, 68% yield). 1H NMR (400 MHz, DMSO-d4): δ 7.67 (m, 1 H), 7.52 (m, 1 H), 7.19 (m, 1 H), 6.89 (m, 1 H), 5.32 (s, 2 H), 1.58 (s, 9 H); MS (ESI) m/z: 190.1 [M+H+].

Workup

  1. customat RT
  2. customfor 2 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-bdb65c10e3cc493f85eac72c4484f590
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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