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

HRID 703990Notes

Reaction equation

HRID 703990 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-1b7dce8ac2c04f6b94eba884ffa2c3d3
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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