Potassium Carbonate → HCID 86677037, compound

HRID 927125Notes

Reaction equation

HRID 927125 reaction equation
N1C=CC=CC=1.C(B1OB(C=C)OB([CH:17]=[CH2:18])O1)=C.[CH2:19]([O:26][C:27]1[N:28]=[N:29][C:30](Cl)=[CH:31][C:32]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH2:19]([O:26][C:27]1[N:28]=[N:29][C:30]([CH:17]=[CH2:18])=[CH:31][C:32]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2×

Product 1

HCID 86677037HCID 86677037, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A vessel containing 2,4,6-triethenyl-1,3,5,2,4,6-trioxatriborinane compound with pyridine (1:1) (1.105 g, 4.59 mmol), 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1, 3 g, 9.18 mmol) and potassium carbonate (3.17 g, 22.95 mmol) was evacuated and flushed with nitrogen. Dioxane (30 ml) and water (3 ml) were added in vacuo and the reaction was degassed before tetrakis(triphenyl-phosphine)palladium(0) (0.530 g, 0.459 mmol) was added. The resulting mixture was then heated at 80° C. for 18 hours and upon cooling, was diluted with ethyl acetate and washed with saturated aqueous sodium carbonate solution. The organics were dried (MgSO4), filtered and solvent removed in vacuo to give a brown oil. This was purified by column chromatography (silica, eluting with 0-30% ethyl acetate in petrol) to afford 3,4-bis(benzyloxy)-6-ethenylpyridazine (1.1 g, 38% yield).

Workup

  1. customwas evacuated
  2. customflushed with nitrogen
  3. additionDioxane (30 ml) and water (3 ml) were added in vacuo
  4. additionwas added
  5. temperatureupon cooling
  6. washwashed with saturated aqueous sodium carbonate solution
  7. dry with materialThe organics were dried (MgSO4)
  8. filtrationfiltered
  9. customsolvent removed in vacuo
  10. customto give a brown oil
  11. customThis was purified by column chromatography (silica, eluting with 0-30% ethyl acetate in petrol)

Sources & evidence

ORD record
ord-f02c947edb1249b5bdbdf840e95bfb98
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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