2-(Methylsulfanyl)-3-nitropyrazolo[1,5-a]pyridine → HCID 19010267, compound

HRID 2253378Notes

Reaction equation

HRID 2253378 reaction equation
[CH3:1][S:2][C:3]1[C:11]([N+:12]([O-])=O)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1>C(O)C.O.C(O)(=O)C.[Zn]>[CH3:1][S:2][C:3]1[C:11]([NH2:12])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1

Participants

6

Reactant 1

HCID 123716362-(Methylsulfanyl)-3-nitropyrazolo[1,5-a]pyridine

Product 1

HCID 19010267HCID 19010267, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-methylthio-3-nitropyrazolo[1,5-a]pyridine (Reference; Heterocycles, 1977, 6, 379) (400 mg) in ethanol (20 mL), water (10 mL), acetic acid (2 mL) was added zinc powder (800 mg) and the reaction mixture was heated and stirred for 30 minutes at 80° C. The insoluble residue was filtered out, water was added to the filtrate and extraction was performed with ethyl acetate, and then the organic extract was washed with saturated aqueous sodium bicarbonate and brine. The organic extract was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure to afford (2-methylthiopyrazolo[1,5-a]pyridin-3-yl)amine as a crude product.

Workup

  1. temperaturethe reaction mixture was heated
  2. filtrationThe insoluble residue was filtered out
  3. additionwater was added to the filtrate and extraction
  4. extractionthe organic extract
  5. washwas washed with saturated aqueous sodium bicarbonate and brine
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4cbc5552e6d8497c802b5f72a09bfa68
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

Loading…