Toluene → 4-Methoxy-3-(2-methylphenoxy)-6-phenylpyridazine

HRID 1821687Notes

Reaction equation

HRID 1821687 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.[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(B(O)O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>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>[CH3:17][O:16][C:4]1[CH:3]=[C:2]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:7]=[N:6][C:5]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 229401366-Chloro-4-methoxy-3-(2-methylphenoxy)pyridazine

Product 1

HCID 229402134-Methoxy-3-(2-methylphenoxy)-6-phenylpyridazineYield 59.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

210 mg (0.837 mmol) of 6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in Example 2 (1), toluene (4 mL) and water (0.5 mL) were mixed, 161 mg (1.32 mmol) of phenylboronic acid, 365 mg (2.64 mmol) of potassium carbonate and 102 mg (0.0879 mmol) of tetrakis(triphenylphosphine)palladium were successively added to the mixture at room temperature, and the resulting mixture was refluxed for 2 hours and 50 minutes. The reaction mixture was allowed to stand at room temperature overnight, the mixture was filtered through Celite, and ethyl acetate and water were added to the filtrate. The organic layer was separated, washed with brine. After drying over anhydrous sodium sulfate, the solvent was removed. The obtained residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=3:1) to obtain 146 mg (0.500 mmol, Yield: 59.7%) of 4-methoxy-3-(2-methylphenoxy)-6-phenylpyridazine.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours and 50 minutes
  2. filtrationthe mixture was filtered through Celite, and ethyl acetate and water
  3. additionwere added to the filtrate
  4. customThe organic layer was separated
  5. washwashed with 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 (eluted with hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-3501dd77793f4ffa97693cad74c43c6d
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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