Stannous chloride dihydrate → HCID 178507356, compound

HRID 1269883Notes

Reaction equation

HRID 1269883 reaction equation
O.O.[Sn](Cl)Cl.[Br:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=2)[NH:9][N:8]=1.S([O-])(O)=O.[Na+]>CN(C)C=O>[Br:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:16])[CH:14]=2)[NH:9][N:8]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 23665763Sodium BisulfiteHCID 178526490HCID 178526490, compound

Product 1

HCID 178507356HCID 178507356, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Tin dichloride dihydrate (846 mg, 3.75 mmol) was added to a solution of 3-bromo-5-nitro-1H-indazole (181 mg, 0.748 mmol) in N,N-dimethylformamide (3 ml), and the resulting mixture was stirred at 70° C. for 1.5 hours. After an aqueous sodium hydrogensulfite solution was added thereto to terminate the reaction, ethyl acetate was added to the reaction mixture and the insoluble material was removed by filtration using Celite. The residue was extracted with ethyl acetate/toluene, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby 3-bromo-1H-indazol-5-amine (110 mg, 69%) was obtained.

Workup

  1. customto terminate
  2. customthe reaction, ethyl acetate
  3. additionwas added to the reaction mixture
  4. customthe insoluble material was removed by filtration
  5. extractionThe residue was extracted with ethyl acetate/toluene
  6. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-bb469aa9059f4abfbaf07b55684cc581
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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