3,6-dichloro-4-methoxypyridazine → HCID 23013667, compound

HRID 2424280Notes

Reaction equation

HRID 2424280 reaction equation
[CH:1]1([C:4]2[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=2[OH:12])[CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[Cl:19][C:20]1[N:21]=[N:22][C:23]([Cl:28])=[CH:24][C:25]=1[O:26][CH3:27]>O1CCOCC1.CS(C)=O>[Cl:28][C:23]1[N:22]=[N:21][C:20]([O:12][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH3:11])[C:4]=2[CH:1]2[CH2:2][CH2:3]2)=[C:25]([O:26][CH3:27])[CH:24]=1.[Cl:19][C:20]1[N:21]=[N:22][C:23]([O:12][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH3:11])[C:4]=2[CH:1]2[CH2:2][CH2:3]2)=[CH:24][C:25]=1[O:26][CH3:27]

Participants

7

Reactant 3

HCID 64013433,6-dichloro-4-methoxypyridazineHCID 22940066HCID 22940066, compoundHCID 23665647Potassium tert-butoxide

Product 2

HCID 22940173HCID 22940173, compoundYield 30.8%HCID 23013667HCID 23013667, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Procedure

In a mixed solvent of 1,4-dioxane (2.5 mL) and dimethylsulfoxide (2.5 mL) was dissolved 190 mg (1.16 mmol) of 2-cyclopropyl-3-methoxyphenol, 146 mg (1.30 mmol) of potassium tert-butoxide was added to the solution and the resulting mixture was stirred for 10 minutes. To the mixture was added 170 mg (0.950 mmol) of 3,6-dichloro-4-methoxypyridazine and the resulting mixture was stirred overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 90.1 mg (0.293 mmol, Yield: 30.8%) of 6-chloro-3-(2-cyclopropyl-3-methoxyphenoxy)-4-methoxypyridazine and 114 mg (0.371 mmol, Yield: 39.1%) of 3-chloro-6-(2-cyclopropyl-3-methoxyphenoxy)-4-methoxypyridazine.

Workup

  1. additionwas added to the solution
  2. stirringthe resulting mixture was stirred overnight
  3. extractionextracted with ethyl acetate
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed
  7. customthe obtained residue was purified by silica gel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient)

Sources & evidence

ORD record
ord-fcef354e9be14d168c25b4174ccc4eb8
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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