Water → 3-Chloro-6-(4-chlorophenyl)pyridazine

HRID 1916542Notes

Reaction equation

HRID 1916542 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](OB(O)O)=[CH:18][CH:17]=1.O>O1CCOCC1>[Cl:8][C:5]1[N:4]=[N:3][C:2]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 17810664p-Chlorophenylboric acid

Product 1

HCID 122575023-Chloro-6-(4-chlorophenyl)pyridazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Under an argon atmosphere a solution of 1.08 g (7.05 mmol) 3,6-dichloro-pyridazin, 10 mL 2 M Na2CO3 solution and 80 mg (0.14 mmol) chlorine(di-2-norbornylphosphino)(2′-dimethylamino-1-1′-biphenyl-2-yl)palladium(II) in 150 mL 1,4-dioxane is heated to 110° C. At this temperature a solution of 1.13 g (7.05 mmol) 4-chlorophenyl-boric acid in 50 mL 1,4-dioxane is added dropwise within 2 h and the reaction mixture is heated for another hour. After cooling it is combined with 100 mL water, extracted with 100 mL EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc/EtOAc 8:2).

Workup

  1. temperaturethe reaction mixture is heated for another hour
  2. temperatureAfter cooling it
  3. extractionextracted with 100 mL EtOAc
  4. dry with materialthe organic phase is dried over Na2SO4
  5. customis purified by chromatography (silica gel, cyc/EtOAc 8:2)

Sources & evidence

ORD record
ord-889f578babdb4fa1bbe4804c23debd18
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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