5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole → 1-(Pyridin-2-ylmethyl)-1H-indazol-5-amine

HRID 1162209Notes

Reaction equation

HRID 1162209 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[N:8]=[CH:7]2)([O-])=O>CO.[Pt](=O)=O>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:9]1[C:10]2[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Participants

4

Reactant 1

HCID 224961495-nitro-1-(pyridin-2-ylmethyl)-1H-indazole

Product 1

HCID 219523661-(Pyridin-2-ylmethyl)-1H-indazol-5-amineYield 95.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole (34 g, 134 mmol) and platinum(IV) oxide (1 g) in methanol (500 ml) was hydrogenated under a 1 bar pressure. After 4 hours (when absorption of hydrogen had stopped), the mixture was filtered on celite. The filtrate was evaporated under reduced pressure. The residue was triturated in ether to give 1-(pyridin-2-ylmethyl)-1H-indazol-5-amine as an off-white solid (28.6 g, 95%); NMR Spectrum (CDCl3) 3.61 (m, 2H), 5.67 (m, 2H), 6.78 (d, 1H), 6.82 (dd, 1H), 6.95 (d, 1H), 7.16 (m, 1H), 7.20 (d, 1H), 7.53 (m, 1H), 7.87 (s, 1H), 8.57 (d, 1H); Mass spectrum MH+ 225.

Workup

  1. customAfter 4 hours (when absorption of hydrogen had stopped)
  2. filtrationthe mixture was filtered on celite
  3. customThe filtrate was evaporated under reduced pressure
  4. customThe residue was triturated in ether

Sources & evidence

ORD record
ord-c1bbda7cec504d158129001ae61caee4
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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