Tributylvinyltin → 6-Ethenylpyridine-3-carbonitrile

HRID 970332Notes

Reaction equation

HRID 970332 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[CH2:10]([Sn](CCCC)(CCCC)C=C)[CH2:11]CC>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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH:10]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1)=[CH2:11]

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 190453106-Ethenylpyridine-3-carbonitrileYield 113.9%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A 100 mL round bottom flask equipped with a condenser was charged with 6-Chloro-nicotinonitrile (500 mg, 3.61 mmol), Pd(PPh3)4 (42 mg, 0.036 mmol), PPh3 (28.4 mg, 0.11 mmol), toluene (20 mL) and tributyl-vinyl-stannane (1.37 g, 4.33 mmol) under argon. The mixture was heated to reflux for three hours, then cooled to RT, quenched with water (12 mL), and extracted with EtOAc (30 mL) three times. The organic layer was combined and dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (5% EtOAc/Hexane) to afford compound 384A as a light yellow oil (535 mg). HPLC retention time=1.43 min. (condition A), M+=131.

Workup

  1. customA 100 mL round bottom flask equipped with a condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux for three hours
  4. customquenched with water (12 mL)
  5. extractionextracted with EtOAc (30 mL) three times
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (5% EtOAc/Hexane)

Sources & evidence

ORD record
ord-fc9987df1a35464e8a09d9196ca4d63b
Source dataset
uspto-grants-2007_12
Patent number
US07312209B2

Reaction notes

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