tert-Butyl 4-(6-nitro-1H-indazol-1-yl)piperidine-1-carboxylate → tert-Butyl 4-(6-amino-1H-indazol-1-yl)piperidine-1-carboxylate

HRID 515378Notes

Reaction equation

HRID 515378 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 68609514tert-Butyl 4-(6-nitro-1H-indazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 68272187tert-Butyl 4-(6-amino-1H-indazol-1-yl)piperidine-1-carboxylateYield 147.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl 4-(6-nitro-1H-indazol-1-yl)piperidine-1-carboxylate (3.00 mmol, 1.04 g) and palladium (10% on C) (0.150 mmol, 0.160 g) in ethanol (30 mL) were stirred under a hydrogen atmosphere at 5 bar for 1 hour. The reaction mixture was filtered and concentrated at reduced pressure to afford the title compound (1.4 g). MS (ESI) m/z 317.2 [M+H]+

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-22b95033f17b4419b262c531c1a65376
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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