Stannous chloride dihydrate → HCID 178508015, compound

HRID 1943880Notes

Reaction equation

HRID 1943880 reaction equation
O.O.Cl[Sn]Cl.[N+:6]([C:9]1[CH:10]=[C:11]2[C:17]([C:18]([F:21])([F:20])[F:19])=[N:16][NH:15][C:12]2=[N:13][CH:14]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[F:21][C:18]([F:19])([F:20])[C:17]1[C:11]2[C:12](=[N:13][CH:14]=[C:9]([NH2:6])[CH:10]=2)[NH:15][N:16]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 178526794HCID 178526794, compound

Product 1

HCID 178508015HCID 178508015, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

SnCl2.2H2O (1.3 g, 5.7 mmol) was added to 5-nitro-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine (0.19 g, 0.82 mmol) in ethyl acetate (20 mL). The resulting solution was heated to reflux for 3 hours. The cooled yellow solution was treated with dilute aqueous sodium bicarbonate. The resulting slurry was filtered through celite, and the filter cake was washed with ethyl acetate. The layers were separated, and the organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to yield 3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine-5-amine (0.17 g, 99%) as a film.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe resulting slurry was filtered through celite
  4. washthe filter cake was washed with ethyl acetate
  5. customThe layers were separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-07064f95df9f46eba7890d07b2c0c679
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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