HCID 86720935, compound → HCID 86720936, compound

HRID 524879Notes

Reaction equation

HRID 524879 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:21]([O-])=O)[C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1>CO.[Zn+2].[Br-].[Br-].[Pd]>[NH2:21][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:12][CH2:13]1

Participants

5

Reactant 1

HCID 86720935HCID 86720935, compound

Product 1

HCID 86720936HCID 86720936, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 10421208Zinc bromideCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(3-chloro-5-nitropyridin-4-yl)piperazine-1-carboxylate (900 mg, 2.626 mmol) and ZnBr2 (118.3 mg, 28.16 μL, 0.5252 mmol) in methanol (27.00 mL) was added Pd on C (10%, wet, Degussa) (300 mg). The reaction mixture was stirred at RT for 4 h under an atmosphere of hydrogen (balloon). The catalyst was filtered off and the filtrate was concentrated in vacuo to yield tert-butyl 4-(3-amino-5-chloropyridin-4-yl)piperazine-1-carboxylate which was used without further purification (820 mg, 99%). MS (ES+) 313.2.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ca6820923466450082d6c89e90c6d781
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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