HCID 67088905, compound → HCID 67089079, compound

HRID 1943866Notes

Reaction equation

HRID 1943866 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[N:4]([S:14]([C:17]2[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[N:3]=1>C(OCC)(=O)C>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[N:4]([S:14]([C:17]2[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=2)(=[O:15])=[O:16])[N:3]=1

Participants

3

Reactant 1

HCID 67088905HCID 67088905, compound

Product 1

HCID 67089079HCID 67089079, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

SnCl2 dihydrate (0.85 g, 3.79 mmol) was added to a suspension of 3-bromo-5-nitro-1-tosyl-1H-indazole (0.300 g, 0.76 mmol) in ethyl acetate (25 mL), and the reaction mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and quenched with saturated NaHCO3 (25 mL). The resulting suspension was filtered through a pad of celite, and the filter cake was washed with ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (1:1) to give 3-bromo-1-tosyl-1H-indazol-5-amine (0.256 g, 92%) as a solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customquenched with saturated NaHCO3 (25 mL)
  4. filtrationThe resulting suspension was filtered through a pad of celite
  5. washthe filter cake was washed with ethyl acetate (100 mL)
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography
  11. washeluting with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-5331db065aa045cea5ce3b2b3832e0d3
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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