Toluene → HCID 72213903, compound

HRID 732395Notes

Reaction equation

HRID 732395 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(C)C=CC=CC=1.C([Sn](CCCC)(CCCC)[C:25]([O:27]CC)=[CH2:26])CCC>C(OCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[C:10]([Cl:12])[N:11]=[C:2]([C:25](=[O:27])[CH3:26])[CH:3]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 93237Methyl 2,6-dichloroisonicotinateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 72213903HCID 72213903, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Add methyl 2,6-dichloroisonicotinate (3.0 g, 15.0 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (105 mg, 0.15 mmol) and toluene (10 mL) in a previously nitrogen filled sealed vessel. Flush the reactants with nitrogen again. Add tributyl(1-ethoxyvinyl)tin (5.57 mL, 16.5 mmol) under nitrogen and heat the sealed mixture at 100° C. overnight with vigorous stirring. Cool the reaction to room temperature, dilute with diethyl ether and filter through a filtering agent. Concentrate to near dryness and dilute the residue with THF (10 mL). Add dropwise 5 N HCl (5 mL) and stir the mixture overnight. Concentrate to near dryness and extract the organic material by diethyl ether, partitioning with water. Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the title compound as a solid over two steps (47%).

Workup

  1. additionfilled
  2. customsealed vessel
  3. customFlush the reactants with nitrogen again
  4. temperatureCool
  5. customthe reaction to room temperature
  6. filtrationfilter through a filtering agent
  7. concentrationConcentrate
  8. additiondilute the residue with THF (10 mL)
  9. additionAdd dropwise 5 N HCl (5 mL)
  10. concentrationConcentrate
  11. extractionextract the organic material by diethyl ether
  12. custompartitioning with water
  13. dry with materialDry (magnesium sulfate)
  14. concentrationconcentrate
  15. custompurify
  16. wash(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-88f0d42a0ac3408080b0cccdf3b930ff
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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