3,4-Bis(4-methoxyphenyl)-6-chloropyridazine → 3,4-Bis(4-methoxyphenyl)-6-phenylpyridazine

HRID 432619Notes

Reaction equation

HRID 432619 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][C:12](Cl)=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.C(Cl)Cl>C1C=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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][C:12]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 125680843,4-Bis(4-methoxyphenyl)-6-chloropyridazineHCID 21908982Water methylene chlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 121138423,4-Bis(4-methoxyphenyl)-6-phenylpyridazineYield 36.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

3,4-Bis(4-methoxyphenyl)-6-chloropyridazine [Eur. J. Med. Chem.-Chimica Therapeutica, 14, 53-60 (1979)] (309.3 mg, 0.95 mmol) was dissolved in benzene (2 ml). Tetrakis(triphenylphosphine)palladium [Pd(Ph3P)4] (90.6 mg, 0.08 mmol) and phenylmagnesium bromide (1.0 M tetrahydrofuran solution) (1.5 ml) were then added successively, followed by stirring at 60° C. for 75 minutes. After water-methylene chloride was added to the reaction mixture, the mixture was extracted with methylene chloride and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was then separated and purified by chromatography on a silica gel column [silica gel (40 g), hexane/ethyl acetate (2/1)], whereby the title compound was obtained as a pale yellow amorphous solid (129 mg, 36.9%)

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off
  4. customthe residue was then separated
  5. custompurified by chromatography on a silica gel column [silica gel (40 g), hexane/ethyl acetate (2/1)], whereby the title compound

Sources & evidence

ORD record
ord-b3638a0bd3904b26a3442cfa33b7aabb
Source dataset
uspto-grants-2003_12
Patent number
US06664256B1

Reaction notes

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