Stannous Chloride → HCID 178508014, compound

HRID 1943907Notes

Reaction equation

HRID 1943907 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=2)[NH:9][N:8]=1.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH2:16])[CH:14]=2)[NH:9][N:8]=1

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 178526792HCID 178526792, compound

Product 1

HCID 178508014HCID 178508014, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 50 ml, round bottom flask was charged with 3-(pyridin-2-yl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (0.10 g, 0.41 mmol) and tin dichloride (1.0 g, 5.2 mmol) in ethyl acetate (10 mL) and methanol (10 mL) and was heated to reflux for 3 hours. The reaction mixture was cooled and poured into saturated aqueous sodium bicarbonate and filtered through celite. The organic layer was separated, dried (MgSO4), and concentrated. The residue was purified by silica gel chromatography eluting with 10-60% methanol in methylene chloride to afford 3-(pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-amine (52 mg, 59% yield) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through celite
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 10-60% methanol in methylene chloride

Sources & evidence

ORD record
ord-be4c12f5371e4cf181819436ca310a55
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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