Sodium hydride → 3-Chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine

HRID 1516203Notes

Reaction equation

HRID 1516203 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].[H-].[Na+].[Cl:17][C:18]1[N:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=1>C1COCC1>[Cl:17][C:18]1[N:19]=[N:20][C:21]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

Product 1

HCID 426297693-Chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazineYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (5.0 g, 26.4 mmol) in THF (50 mL) was added sodium hydride (55% dispersion in mineral oil, 1.27 g, 29.1 mmol). The mixture was stirred at room temperature for 30 min. After addition of 3,6-dichloropyridazine (4.33 g, 29.1 mmol) the mixture was stirred at room temperature for another 5 h. Then the mixture was evaporated, extracted (ethyl acetate/water) and the organic phase was dried with sodium sulfate and concentrated. Chromatography (SiO2, heptane:ethyl acetate=100:0 to 70:30) afforded the title compound (6.62 g, 83%) as a white solid. MS: m/e=302.0 [M+H]+.

Workup

  1. stirringwas stirred at room temperature for another 5 h
  2. customThen the mixture was evaporated
  3. extractionextracted (ethyl acetate/water)
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d3789a121c29474abfa611967fc795c3
Source dataset
uspto-grants-2012_07
Patent number
US08227461B2

Reaction notes

Loading…