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

HRID 1916669Notes

Reaction equation

HRID 1916669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](OB(O)O)=[CH:4][CH:3]=1.[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:12][C:13]1[N:14]=[N:15][C:16]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
110 °C

Procedure

Under an argon atmosphere a solution of 11.3 g (70.5 mmol) 4-chlorophenylboric acid in 50 mL 1,4-dioxane is added to a solution of 10.8 g (70.5 mmol) 3,6-dichloropyridazine, 10 mL (20 mmol) of a 2 M Na2CO3 solution and 600 mg (0.73 mmol) Pd(dppf)Cl2 in 150 mL 1,4-dioxane at 110° C. over 2 h. The reaction mixture is stirred for 1 h at 110° C. 100 mL water are added and the aqueous phase is extracted with 100 mL EtOAc. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Purification is carried out by column chromatography on silica gel (cyc/EtOAc 4:1).

Workup

  1. extractionthe aqueous phase is extracted with 100 mL EtOAc
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customPurification

Sources & evidence

ORD record
ord-a430230f263740108de0b58181b385bd
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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