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

HRID 1916674Notes

Reaction equation

HRID 1916674 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-b841da7b84814a379a6b0c6a8e1534bf
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…