Toluene → 3-methoxy-6-phenylpyridazine

HRID 1359400Notes

Reaction equation

HRID 1359400 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:10]1(OB(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O1CCCC1.CO>[C:10]1([C:2]2[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 744033-Chloro-6-methoxypyridazineHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 110845673-methoxy-6-phenylpyridazineYield 46.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3.0 g of 3-chloro-6-methoxypyridazine, 3.8 g of phenylboric acid, 2.4 g of tetrakis(triphenylphosphine)palladium(0), 160 ml of toluene, 40 ml of methanol, 80 ml of an aqueous 2 mol sodium carbonate solution and 30 ml of tetrahydrofuran was stirred under heating at 85° C. for one hour. After cooling as it was, the reaction solution was extracted with ethyl acetate. The organic phase was washed with brine and eluted with ethyl acetate through NH-silica gel (Fuji Silicia). After removing the solvent, the residue was crystallized, to give 1.8 g of the target compound.

Workup

  1. temperatureAfter cooling as it
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. washeluted with ethyl acetate through NH-silica gel (Fuji Silicia)
  5. customAfter removing the solvent
  6. customthe residue was crystallized

Sources & evidence

ORD record
ord-26eca490dccb4f7ca2d1318e11d3fc19
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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