Water → 2-benzyl-5-chloro-4-(4-chlorophenyl)pyridazin-3(2H)-one

HRID 2224251Notes

Reaction equation

HRID 2224251 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12](Cl)=[C:11]([Cl:16])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=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>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)=[C:11]([Cl:16])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 7224382-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one

Product 1

HCID 597168732-benzyl-5-chloro-4-(4-chlorophenyl)pyridazin-3(2H)-oneYield 30.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-benzyl-4,5-dichloropyridazin-3(2H)-one (30.6 g, 120 mmol), prepared as described in Example 244A, 4-chlorophenyl boronic acid (20.6 g, 132 mmol) and tetrakis(triphenylphosphine)palladium (5 g, 4.3 mmol) in toluene (300 mL) under an atmosphere of argon, and was added an aqueous Na2CO3 solution (2M, 66 mL, 132 mmol). The reaction mixture was stirred at 100° C. under argon for 16 h. The reaction was then allowed to cool to RT and was subsequently poured into water (200 mL). The resulting mixture was extracted with EtOAc (3×150 mL). The combined organic layers were washed with saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The obtained thick syrup was dissolved in MeOH (100 mL) and the resulting solution kept at 0° C. until white solid precipitated. The solid was collected by filtration, washed with hexanes, and then triturated with EtOAc-hexanes to give the title compound, 2-benzyl-5-chloro-4-(4-chlorophenyl)pyridazin-3(2H)-one (12 g, 30%) as a white powder. LC/MS (method A, general procedure): RT=3.81 min, (M+H)+=331.

Workup

  1. customprepared
  2. temperatureto cool to RT
  3. extractionThe resulting mixture was extracted with EtOAc (3×150 mL)
  4. washThe combined organic layers were washed with saturated aqueous NaCl
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe obtained thick syrup was dissolved in MeOH (100 mL)
  9. customkept at 0° C. until white solid
  10. customprecipitated
  11. filtrationThe solid was collected by filtration
  12. washwashed with hexanes
  13. customtriturated with EtOAc-hexanes

Sources & evidence

ORD record
ord-8c444740c62d458582ed9578f5316069
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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