Sodium Carbonate → HCID 66707657, compound

HRID 1890225Notes

Reaction equation

HRID 1890225 reaction equation
O1CCOCC1.Cl[C:8]1[C:9](=[O:17])[N:10]([CH3:16])[N:11]=[CH:12][C:13]=1[O:14][CH3:15].[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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.O>[CH3:15][O:14][C:13]1[CH:12]=[N:11][N:10]([CH3:16])[C:9](=[O:17])[C:8]=1[C:20]1[C:21]([CH3:26])=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=1[CH3:18]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 27749384-Chloro-5-methoxy-2-methyl-2,3-dihydropyridazin-3-one

Product 1

HCID 66707657HCID 66707657, compoundYield 37.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

To a mixture of 55 ml of dioxane and 17 ml of water were added 1.38 g of 4-chloro-5-methoxy-2-methyl-3(2H)-pyridazinone, 1.55 g of 2,4,6-trimethylphenylboronic acid, 1.86 g of sodium carbonate, 2.53 g of tetrabutylammonium bromide and 0.38 g of tetrakis(triphenylphosphine)palladium. This mixture was heated under reflux for 32 hours under a nitrogen atmosphere. A part of the reaction mixture was evaporated. To the resultant concentrate, 150 ml of water was added, followed by extraction with ethyl acetate (twice). The organic layer was washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 0.77 g of 5-methoxy-2-methyl-4-(2,4,6-trimethylphenyl)-3(2H)-pyridazinone [compound (V-2-1)] as a white crystal. Melting point: 186 to 192° C.

Workup

  1. temperatureThis mixture was heated
  2. temperatureunder reflux for 32 hours under a nitrogen atmosphere
  3. customA part of the reaction mixture was evaporated
  4. concentrationTo the resultant concentrate
  5. addition150 ml of water was added
  6. extractionfollowed by extraction with ethyl acetate (twice)
  7. washThe organic layer was washed with an aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1494aee14e24a7d89fd8582b4623df2
Source dataset
uspto-grants-2013_08
Patent number
US08507410B2

Reaction notes

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