Stannous Chloride → HCID 57527205, compound

HRID 1671822Notes

Reaction equation

HRID 1671822 reaction equation
[CH2:1]([S:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[C:6]([C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])=[N:15][N:16]([CH3:18])[CH:17]=2)[N:5]=1)[CH3:2].Cl[Sn]Cl>CCOC(C)=O>[CH2:1]([S:3][C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:6]([C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])=[N:15][N:16]([CH3:18])[CH:17]=2)[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 57527201HCID 57527201, compound

Product 1

HCID 57527205HCID 57527205, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(ethylthio)-6-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-3-nitropyridine (2.87 g, 8.01 mmol, 1.00 eq.) and SnCl2●2H2O (9.05 g, 40.1 mmol, 5.0 eq.) in EtOAc (200 mL) was refluxed for 2 h. After cooling to room temperature, the solution was washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo to give 2-(ethylthio)-6-(3-(2-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)pyridine-3-amine as a yellow solid (2.31 g, 88% yield).

Workup

  1. washthe solution was washed with saturated aqueous NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a537e3bdde64c27bc6df71f182b87bd
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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