3,4-Bis(4-methoxyphenyl)-6-chloropyridazine → HCID 18760037, compound

HRID 432661Notes

Reaction equation

HRID 432661 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.[CH2:24]([Mg]Br)[CH:25]=[CH2:26].O.C(OCC)(=O)C>O1CCCC1.C(OCC)C.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>[CH2:26]([C:12]1[N:11]=[N:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[C:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH:13]=1)[CH:25]=[CH2:24]

Participants

7

Reactant 3

HCID 125680843,4-Bis(4-methoxyphenyl)-6-chloropyridazineHCID 22728543Water ethylacetateHCID 178455850HCID 178455850, compound

Product 1

HCID 18760037HCID 18760037, compoundYield 69.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-bis(4-methoxyphenyl)-6-chloropyridazine 1.2 g (3.7 mmol) in tetrahydrofuran (24 ml), tetrakis(triphenylphosphine)palladium (0.21 g, 0.18 mmol) was added. Under cooling with ice water under an argon gas atmosphere, a 1 M solution (11 ml) of allylmagnesium bromide in diethyl ether was added dropwise. After the resulting mixture was stirred at the same temperature for 1 hour, the temperature of the mixture was allowed to rise to room temperature, followed by further stirring for 2 hours. Water-ethyl acetate was added to the reaction mixture, and the thus-obtained mixture was extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The extract was concentrated under reduced pressure and the residue was left over at room temperature for 3 days. The residue was separated and purified by chromatography on a silica gel column [hexane/ethyl acetate (4/1)], whereby the title compound was obtained as a pale brown oil (0.85 g, 69.8%).

Workup

  1. customto rise to room temperature
  2. stirringby further stirring for 2 hours
  3. extractionthe thus-obtained mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe extract was concentrated under reduced pressure
  7. waitthe residue was left over at room temperature for 3 days
  8. customThe residue was separated
  9. custompurified by chromatography on a silica gel column [hexane/ethyl acetate (4/1)], whereby the title compound

Sources & evidence

ORD record
ord-609d768583ed495990a988e00f332c6c
Source dataset
uspto-grants-2003_12
Patent number
US06664256B1

Reaction notes

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