2-Bromo-6-methoxypyridine → 2-Methoxy-6-vinylpyridine

HRID 2390793Notes

Reaction equation

HRID 2390793 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.[CH2:10](C([Sn])=C(CCCC)CCCC)[CH2:11]CC>O1CCOCC1>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:10]=[CH2:11])[N:3]=1

Participants

4

Reactant 2

HCID 2568102-Bromo-6-methoxypyridineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 190915662-Methoxy-6-vinylpyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

step 1—A mixture of 2-bromo-6-methoxypyridine (5.00 g), tributylvinyltin (9.30 mL), and PdCl2(PPh)3 in dioxane (100 mL) in a sealed tube was heated overnight at 100° C. The reaction was cooled to RT and the volatile organics were removed under reduced pressure. The crude residue was purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (0 to 10% EtOAc) to afford 2.00 g of 2-methoxy-6-vinyl-pyridine (24) as a colorless oil.

Workup

  1. temperatureThe reaction was cooled to RT
  2. customthe volatile organics were removed under reduced pressure
  3. customThe crude residue was purified by SiO2 chromatography
  4. washeluting with a EtOAc/hexane gradient (0 to 10% EtOAc)

Sources & evidence

ORD record
ord-079bca40aad340ed93ad83ee4b9eafb6
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

Loading…