5-Bromo-2-ethylpyridine → 2-Ethyl-5-vinylpyridine

HRID 1045523Notes

Reaction equation

HRID 1045523 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][N:4]=1)[CH3:2].[CH2:10](C([Sn])=C(CCCC)CCCC)[CH2:11]CC>CN(C=O)C.C1COCC1.O.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>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:10]=[CH2:11])=[CH:5][N:4]=1)[CH3:2]

Participants

6

Reactant 2

HCID 139797365-Bromo-2-ethylpyridineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 151623692-Ethyl-5-vinylpyridineYield 93.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The title compound was prepared by following general procedure 2. 2-Ethyl-5-bromo-pyridine (0.6 g, 0.00322 mol) was dissolved in DMF:THF (3:1 6 mL), and to this solution, tributylvinyltin (1.03 mL, 0.00354 mol) and Pd(PPh3)4 (0.048 g, 0.000041 mol) were added at RT under nitrogen and the mixture heated at 100° C. for 30 min. After completion of the reaction (TLC), the reaction mixture was cooled to RT and diluted with water (60 mL) and extracted with DCM (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure using rotary evaporator below 40° C. The crude was purified through column chromatography (2% ethylacetate:hexane in silica 100-200 mesh, Diameter of column—5.0 cm, Height of silica—approx. 5 inch) to provide 2-ethyl-5-vinylpyridine as a light yellow liquid (0.4 g, 93% yield).

Workup

  1. customThe title compound was prepared
  2. customAfter completion of the reaction (TLC)
  3. temperaturethe reaction mixture was cooled to RT
  4. extractionextracted with DCM (3×100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customevaporator below 40° C
  8. customThe crude was purified through column chromatography (2% ethylacetate:hexane in silica 100-200 mesh, Diameter of column—5.0 cm, Height of silica—approx. 5 inch)

Sources & evidence

ORD record
ord-f84ab9f6275b46b8b5c83917b130a997
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

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