Stannous chloride dihydrate → HCID 67088915, compound

HRID 1943903Notes

Reaction equation

HRID 1943903 reaction equation
O.O.Cl[Sn]Cl.[N:6]1([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[NH:13][N:12]=2)[CH:10]=[CH:9][N:8]=[CH:7]1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[N:6]1([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([NH2:20])[CH:18]=3)[NH:13][N:12]=2)[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 67089020HCID 67089020, compound

Product 1

HCID 67088915HCID 67088915, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

SnCl2.2H2O (1.03 g, 4.56 mmol) was added to 3-(1H-imidazol-1-yl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (210 mg, 0.912 mmol) in ethyl acetate (100 mL). The mixture was heated to reflux for 1 hour. The cooled reaction mixture was diluted with ethyl acetate and treated dropwise with saturated aqueous sodium bicarbonate. The slurry was stirred for 30 minutes and then filtered through celite. The filtrate was washed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and evaporated to yield 3-(1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-5-amine (90 mg, 49% yield) as a solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customThe cooled reaction mixture
  4. filtrationfiltered through celite
  5. washThe filtrate was washed with saturated aqueous sodium bicarbonate, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-b1a05ede8559496c9a8c584bc452c21e
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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