Sodium Methoxide → 3-(3-Methoxypyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine

HRID 466029Notes

Reaction equation

HRID 466029 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:6]=[N:7][C:8]([C:11]2[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=23)=[CH:9][CH:10]=1>CO>[CH3:1][O:2][C:5]1[N:6]=[N:7][C:8]([C:11]2[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=23)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 151581443-(3-Chloropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 151581493-(3-Methoxypyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methoxide in methanol (28%, 411 mg) was added to a mixture of 3-(3-chloropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (436 mg) and methanol (4 ml) at room temperature. The reaction mixture was heated under reflux for 3 hours. After evaporating the solvent in vacuo, a saturated aqueous solution of sodium chloride (20 ml) was added to the residue and extracted with chloroform (20 ml×3). The combined extract was washed with a saturated aqueous solution of sodium chloride (20 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (10 g) using chloroform as an eluent and recrystallized from 95% EtOH to give 3-(3-methoxypyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (165 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter evaporating the solvent in vacuo
  4. additiona saturated aqueous solution of sodium chloride (20 ml) was added to the residue
  5. extractionextracted with chloroform (20 ml×3)
  6. extractionThe combined extract
  7. washwas washed with a saturated aqueous solution of sodium chloride (20 ml)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel (10 g)
  11. customrecrystallized from 95% EtOH

Sources & evidence

ORD record
ord-d67a5835c85e41a485e8181b4f58e265
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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