Ethanol → HCID 21084112, compound

HRID 347840Notes

Reaction equation

HRID 347840 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:13]([N+:14]([O-])=O)=[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([Br:12])[N:6]2[N:5]=1.C(O)C.O>[Zn].C(O)(=O)C>[Br:12][C:11]1[N:6]2[N:5]=[C:4]([CH2:3][O:2][CH3:1])[C:13]([NH2:14])=[C:7]2[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 21084116HCID 21084116, compound

Product 1

HCID 21084112HCID 21084112, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of (7-bromo-3-nitropyrazolo[1,5-a]pyridin-2-yl)methyl methyl ether (540 mg) in a mixed solution of ethanol (10 mL), water (5 mL) and acetic acid (1 mL) was added zinc powder (540 mg), and the reaction mixture was heated and stirred for 30 minutes at 60° C. After filtering off insoluble residue, water was added to the filtrate, extraction was performed with ethyl acetate and the organic extract was washed with saturated aqueous sodium bicarbonate and brine. The obtained organic extract was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography and 7-bromo-2-(methoxymethyl)pyrazolo[1,5-a]pyridine-3-amine (371 mg) was obtained as a brown oil from the n-hexane:ethyl acetate (2:1) fraction.

Workup

  1. temperaturethe reaction mixture was heated
  2. filtrationAfter filtering off insoluble residue, water
  3. additionwas added to the filtrate, extraction
  4. extractionthe organic extract
  5. washwas washed with saturated aqueous sodium bicarbonate and brine
  6. extractionThe obtained organic extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-50fb1a455dbf4336a5f5b91a46a0ece1
Source dataset
uspto-grants-2007_02
Patent number
US07176216B2

Reaction notes

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