6-nitro-1H-indazol-3-yl 4-methylpiperidine-1-carboxylate → 6-Amino-1H-indazol-3-yl 4-methylpiperidine-1-carboxylate

HRID 490310Notes

Reaction equation

HRID 490310 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([N+:20]([O-])=O)=[CH:17][CH:18]=3)[NH:13][N:12]=2)=[O:9])[CH2:4][CH2:3]1>C(O)C.[Pd]>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([NH2:20])=[CH:17][CH:18]=3)[NH:13][N:12]=2)=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 670827616-nitro-1H-indazol-3-yl 4-methylpiperidine-1-carboxylate

Product 1

HCID 115073446-Amino-1H-indazol-3-yl 4-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

30 mg (0.1 mmol) of 6-nitro-1H-indazol-3-yl 4-methylpiperidine-1-carboxylate (Example 5B) in 15 ml of ethanol were hydrogenated in the presence of 10% palladium/carbon under a hydrogen pressure of 2 bar at room temperature for 2.5 h. The catalyst was filtered off with suction, and the filtrate was concentrated. Yield: 21 mg (76%), M+H+: 275.2.

Workup

  1. customat room temperature
  2. customfor 2.5 h
  3. filtrationThe catalyst was filtered off with suction
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3e775771a57d40f68ffd3f8c572af320
Source dataset
uspto-grants-2009_05
Patent number
US07528155B2

Reaction notes

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