Tributylvinyltin → HCID 74890377, compound

HRID 627751Notes

Reaction equation

HRID 627751 reaction equation
Br[C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:11]([Sn](CCCC)(CCCC)C=C)[CH2:12]CC>O.CCOC(C)=O.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>[Cl:8][C:6]1[CH:7]=[C:2]([CH:11]=[CH2:12])[C:3]([C:9]#[N:10])=[N:4][CH:5]=1

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 225912463-Bromo-5-chloropyridine-2-carbonitrile

Product 1

HCID 74890377HCID 74890377, compoundYield 67.9%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A microwave vial was charged with 3-bromo-5-chloropicolinonitrile (1.40 g, 6.44 mmol) and dichlorobis(triphenyl-phosphine)palladium (II) (0.54 g, 0.77 mmol). The vial was evacuated and backfilled with nitrogen and 1,4-dioxane (10 mL) was added, followed by tri-n-butyl(vinyl)tin (2.45 mL, 7.73 mmol). The reaction mixture was heated at 100° C. for 1 h. The reaction mixture was diluted with water and EtOAc. The solvent was removed under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 10% to 50% EtOAc in hexane, to provide 5-chloro-3-vinylpicolinonitrile (0.72 g, 4.37 mmol, 67.9% yield) as white solid.

Workup

  1. customThe vial was evacuated
  2. additionwas added
  3. customThe solvent was removed under reduced pressure
  4. customThe crude material was absorbed onto a plug of silica gel
  5. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (40 g)
  6. washeluting with a gradient of 10% to 50% EtOAc in hexane

Sources & evidence

ORD record
ord-a065fda123f849538a02705733451059
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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