Stannous Chloride → 2-Bromo-5-(4-chloro-phenyl)-pyridin-3-ylamine

HRID 271707Notes

Reaction equation

HRID 271707 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 859696992-Bromo-5-(4-chlorophenyl)-3-nitropyridine

Product 1

HCID 859697042-Bromo-5-(4-chloro-phenyl)-pyridin-3-ylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.60 g (17.9 mmol) 2-bromo-5-(4-chloro-phenyl)-3-nitro-pyridine, 20.3 g (90.0 mmol) tin(II)-chloride and 18.9 g (225 mmol) NaHCO3 in 300 mL EtOAc is refluxed for 30 h. After filtration the solvent is eliminated i.vac. The residue is triturated with DCM and after filtration the filter residue is dried in the air.

Workup

  1. filtrationAfter filtration the solvent
  2. customThe residue is triturated with DCM
  3. filtrationafter filtration the filter residue
  4. customis dried in the air

Sources & evidence

ORD record
ord-42d186145eb540ad80ecea9f5e9ad76f
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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