Stannous Chloride → 3-chloro-6-fluoro-1H-indazol-5-amine

HRID 734704Notes

Reaction equation

HRID 734704 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:14])=[C:8]([N+:11]([O-])=O)[CH:9]=2)[NH:4][N:3]=1.Cl[Sn]Cl>CCO.CCOC(C)=O.[OH-].[Na+]>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:14])=[C:8]([NH2:11])[CH:9]=2)[NH:4][N:3]=1

Participants

6

Reactant 2

HCID 24479Stannous ChlorideHCID 1785264023-Chloro-6-fluoro-5-nitro-1H-indazole

Product 1

HCID 1785072033-chloro-6-fluoro-1H-indazol-5-amineYield 51%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

The product from Step 1 (575 mg, 2.667 mmol, 1.0 equiv) was dissolved in 15 mL EtOH and SnCl2 (2.5 g, 13.337 mmol, 5.0 equiv) was added. The reaction mixture was heated to 70° C. for 4 hours. The reaction mixture was diluted with EtOAc and 6N NaOH, filtered through a pad of celite and washed with EtOAc and water. The phases of the filtrate were separated, and the organic phase was washed once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (20-100% EtOAc in Hexanes) to provide 250 mg (51%) of the title compound as a yellow solid. MS (ES+) m/e 186 [M+H]+

Workup

  1. filtrationfiltered through a pad of celite
  2. washwashed with EtOAc and water
  3. customThe phases of the filtrate were separated
  4. washthe organic phase was washed once with satd
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated en vacuo
  8. customThe residue was purified by flash chromatography (20-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-14000d11bff8489c881b3423da4506b7
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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