5-Bromopyridine-2-carboxylic acid → 5-Ethenylpyridine-2-carboxylic acid

HRID 1045532Notes

Reaction equation

HRID 1045532 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH2:11](C([Sn])=C(CCCC)CCCC)[CH2:12]CC>O1CCOCC1.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>[CH:11]([C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1)=[CH2:12]

Participants

5

Reactant 2

HCID 6085445-Bromopyridine-2-carboxylic acidHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 230615385-Ethenylpyridine-2-carboxylic acidYield 94.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by following general procedure 2. To a solution of 5-bromo pyridine-2-carboxylic acid (5 g, 24.75 mmol) in 50 mL of 1,4-dioxan, dichlorobis(triphenylphosphine)palladium(II) (2.08 g, 2.96 mmol) was added at RT and stirred at RT for 5 min. Tributylvinyltin (11.7 g, 36.9 mmol) was added slowly at RT and stirred at 100° C. for 3 h. The reaction mixture was monitored by TLC and LCMS. After completion of the starting material, evaporated the solvent below 40° C. and purified by column chromatography using ethyl acetate to afford the 5-vinylpyridine-2-carboxylic acid (3.5 g, 94.5%).

Workup

  1. customThe title compound was prepared
  2. stirringstirred at 100° C. for 3 h
  3. customAfter completion of the starting material, evaporated the solvent below 40° C.
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-4cb84c0a18214ebaad2ee3f790bfc81f
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

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