Sodium Methoxide → 3-Methoxy-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine

HRID 548815Notes

Reaction equation

HRID 548815 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1.[CH3:22][O-:23].[Na+]>CO.C1COCC1>[CH3:22][O:23][C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 426297693-Chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine

Product 1

HCID 426305013-Methoxy-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazineYield 28.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine (200 mg, 0.66 mmol) in a mixture of methanol (3 mL) and THF (1 mL) was added dropwise sodium methoxide (5.4 M in MeOH, 0.16 mL, 0.86 mmol) and the reaction mixture was heated under reflux for 24 h. After dilution with tert-butylmethylether (4 mL) and water (2 mL) it was extracted with tert-butylmethylether (15 mL) and dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (56 mg, 27%) as a colorless oil. MS: m/e=298.3 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 24 h
  3. extractionAfter dilution with tert-butylmethylether (4 mL) and water (2 mL) it was extracted with tert-butylmethylether (15 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

Sources & evidence

ORD record
ord-344499417ca14e7d9e54633bba35ba73
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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