Sodium Fluoride → HCID 23013753, compound

HRID 1821686Notes

Reaction equation

HRID 1821686 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[C:4]([O:16][CH3:17])[CH:3]=1.[CH2:18]([O:20][C:21]([Sn](CCCC)(CCCC)CCCC)=[CH2:22])[CH3:19].C(OCC)(=O)C.[F-].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:21]([O:20][C:18]([C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[C:4]([O:16][CH3:17])[CH:3]=1)=[CH2:19])[CH3:22]

Participants

8

Reactant 4

HCID 5235Sodium FluorideHCID 8857Ethyl AcetateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 229401366-Chloro-4-methoxy-3-(2-methylphenoxy)pyridazine

Product 1

HCID 23013753HCID 23013753, compoundYield 14.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In toluene (6.5 mL) was dissolved 321 mg (1.28 mmol) of 6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in Example 2 (1), 534 mg (1.48 mmol) of (1-ethoxyvinyl)(tributyl)tin, then 155.3 mg (0.134 mmol) of tetrakis(triphenylphosphine)palladium were successively added to the solution at room temperature, and the resulting mixture was refluxed for 3 hours and 20 minutes. The reaction mixture was allowed to stand at room temperature overnight, then, ethyl acetate, water and sodium fluoride were added to the mixture and the resulting mixture was stirred for 2 hours. The mixture was filtered through Celite, ethyl acetate was added to the filtrate, and the organic layer was separated, and washed successively with water and brine. After drying over anhydrous sodium sulfate, the solvent was removed. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate, gradient) to obtain 51.8 mg (0.181 mmol, Yield: 14.1%) of 6-(1-ethoxyvinyl)-4-methoxy-3-(2-methylphenoxy)pyridazine.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours and 20 minutes
  2. filtrationThe mixture was filtered through Celite, ethyl acetate
  3. additionwas added to the filtrate
  4. customthe organic layer was separated
  5. washwashed successively with water and brine
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe solvent was removed
  8. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate, gradient)

Sources & evidence

ORD record
ord-e463b1fadd684163bff933e5f4007af4
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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