Sodium Carbonate → 3-methoxy-6-phenylpyridazine

HRID 1787500Notes

Reaction equation

HRID 1787500 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>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>[CH3:9][O:8][C:5]1[N:4]=[N:3][C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 744033-Chloro-6-methoxypyridazine

Product 1

HCID 110845673-methoxy-6-phenylpyridazineYield 74%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-chloro-6-methoxy-pyridazine (4.0 g, 27.7 mmol) and phenyl boronic acid (5.1 g, 41.6 mmol) in toluene (160 mL) was degassed and tetrakis(triphenylphosphine)palladium (960 mg, 0.83 mmol) and 2M sodium carbonate (29.3 mL, 58.7 mmol) were added. The mixture was heated to reflux under nitrogen for 6 h, then cooled and the organic phase washed with 2M NaOH (75 mL), dried over magnesium sulphate and solvent removed under reduced pressure to give a solid which was subjected to column chromatography (n-Hex/EtOAc 9:1 to 1:1) to afford the title compound (74% yield) as a white solid.

Workup

  1. customwas degassed
  2. temperatureThe mixture was heated
  3. temperatureto reflux under nitrogen for 6 h
  4. temperaturecooled
  5. washthe organic phase washed with 2M NaOH (75 mL)
  6. dry with materialdried over magnesium sulphate and solvent
  7. customremoved under reduced pressure
  8. customto give a solid which

Sources & evidence

ORD record
ord-80bffb68cdb44c56b129e034c7e2266f
Source dataset
uspto-grants-2009_03
Patent number
US07511038B2

Reaction notes

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