Sodium Methoxide → HCID 15158146, compound

HRID 703989Notes

Reaction equation

HRID 703989 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:13][N:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=12>>[CH3:1][O:2][C:5]1[N:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:13][N:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=12

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 15158134HCID 15158134, compound

Product 1

HCID 15158146HCID 15158146, compound

Procedure

To a 28% methanolic solution of sodium methoxide (3 ml) was added 3-(3-chloropyridazin-4-yl)-2-phenylpyrazolo[1.5-a]pyridine (0.61 g). The mixture was refluxed for an hour and evaporated in vacuo. The residue was dissolved in chloroform (20 ml). The chloroform solution was washed with water (5 ml) and a saturated aqueous solution of sodium chloride (5 ml) and dried over magnesium sulfate. The solvent was removed and chromatographed on silica gel (10 g) with n-hexane-ethyl acetate as an eluent. The fractions containing the object compound were combined, evaporated in vacuo, and then recrystallized from a mixture of ethyl acetate and n-hexane to give 3-(3-methoxypyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.30 g).

Workup

  1. temperatureThe mixture was refluxed for an hour
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in chloroform (20 ml)
  4. washThe chloroform solution was washed with water (5 ml)
  5. dry with materiala saturated aqueous solution of sodium chloride (5 ml) and dried over magnesium sulfate
  6. customThe solvent was removed
  7. customchromatographed on silica gel (10 g) with n-hexane-ethyl acetate as an eluent
  8. additionThe fractions containing the object compound
  9. customevaporated in vacuo
  10. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-5f24b9cfafe54523944119531c0aa260
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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