4-Vinylpyridine → HCID 22607319, compound

HRID 2307753Notes

Reaction equation

HRID 2307753 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[CH2:10].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2](/[CH:10]=[CH:9]/[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 693693,5-DibromopyridineHCID 80271Tri-o-tolylphosphine

Product 1

HCID 22607319HCID 22607319, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 3,5-dibromopyridine (5.56 g, 23.4 mmol), 4-vinylpyridine (5.1 mL), palladium acetate (1.05 g), tri-o-tolylphosphine (5.00 g) and triethylamine (33 mL) in acetonitrile (100 mL) was heated overnight at 80° C. and concentrated. The residue was partitioned between 5% NaHCO3 and dichloromethane and filtered. The filtrate was separated and the organic layer was washed with water, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4% methanol/dichloromethane to provide the desired product (2.18 g, 36%). (DCI/NH3) m/e 261, 263 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between 5% NaHCO3 and dichloromethane
  3. filtrationfiltered
  4. customThe filtrate was separated
  5. washthe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by flash column chromatography on silica gel with 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-0cf1e474c2d04d95963c2f1308d11c37
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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