3,6-Dichloropyridazine → 3-Chloro-6-(2,6-difluorobenzyl)pyridazine

HRID 1454962Notes

Reaction equation

HRID 1454962 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[Br-].[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=1[CH2:13][Zn+]>C1COCC1.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>[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:13][C:12]2[C:11]([F:10])=[CH:18][CH:17]=[CH:16][C:15]=2[F:19])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 673313,6-DichloropyridazineHCID 178505728HCID 178505728, compound

Product 1

HCID 575312393-Chloro-6-(2,6-difluorobenzyl)pyridazineYield 47.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,6-dichloro pyridazine (7.39 g, 50 mmol) and tetrakis(triphenylphosphine)palladium (2.89 g, 2.5 mmol) in THF (500 mL) was added 2,6 difluoro benzyl zinc bromide (120 mL, 60 mmol). The reaction mixture was heated to 80° C. for 1.5 hours until the reaction was complete by TLC. The reaction was cooled to room temperature, filtered through celite, and concentrated in vacuo. The crude residue was recrystalized from ether to yield 5.7 g of the title compound.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was recrystalized from ether

Sources & evidence

ORD record
ord-e439f29fbc714d119ad8d5fca1ddaff8
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

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