Triphenylphosphine → HCID 86081346, compound

HRID 732389Notes

Reaction equation

HRID 732389 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].[C:13]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:14]=1.C([Sn](CCCC)(CCCC)C=C)CCC>C1(C)C=CC=CC=1.C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([CH:13]=[CH2:14])[N:11]=[C:10]([Cl:12])[CH:9]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 93237Methyl 2,6-dichloroisonicotinate

Product 1

HCID 86081346HCID 86081346, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Add methyl 2,6-dichloro-isonicotinate (3.8 g, 18.4 mmol), tetrakis(triphenylphosphine)palladium (0) (1.15 g, 0.99 mmol), triphenylphosphine (524 mg, 2 mmol) in toluene (40 mL) to a previously nitrogen-filled sealed vessel. Flush the reactants with nitrogen again. Add tributyl(vinyl)tin (6.98 mL, 24.0 mmol) and heat the sealed mixture at 95° C. overnight. Cool to room temperature, dilute with diethyl ether and filter through a filtering agent. Wash the organic filtrate with saturated ammonium chloride, saturated sodium bicarbonate and saturated aqueous sodium chloride. Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 5:95 to 10:90 ethyl acetate:hexanes) to give the title compound (70%).

Workup

  1. additionfilled
  2. customsealed vessel
  3. customFlush the reactants with nitrogen again
  4. filtrationfilter through a filtering agent
  5. washWash the organic filtrate with saturated ammonium chloride, saturated sodium bicarbonate and saturated aqueous sodium chloride
  6. dry with materialDry (magnesium sulfate)
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 5:95 to 10:90 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-fbdd256710704235b4c7ddc9980b3b89
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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