2-Fluoro-3-iodopyridine → Pyridine, 3,3′-(1Z)-1,2-ethenediylbis[2-fluoro-, (Z)-

HRID 362221Notes

Reaction equation

HRID 362221 reaction equation
[F:1][C:2]1[C:7](/[CH:8]=[CH:9]\[Sn](CCCC)(CCCC)CCCC)=[CH:6][CH:5]=[CH:4][N:3]=1.[F:23][C:24]1[C:29](I)=[CH:28][CH:27]=[CH:26][N:25]=1>C1(C)C=CC=CC=1.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>[F:23][C:24]1[C:29](/[CH:9]=[CH:8]\[C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 2

HCID 70095012-Fluoro-3-iodopyridineHCID 67598837HCID 67598837, compound

Product 1

HCID 22942261Pyridine, 3,3′-(1Z)-1,2-ethenediylbis[2-fluoro-, (Z)-

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Z-2-fluoro-3-(2-tributylstannylethenyl)pyridine (1.39 g), 2-fluoro-3-iodopyridine (0.75 g) and bis(triphenylphosphine)palladium dichloride (0.010 g) in toluene (20 mL) was refluxed under argon for 4 hours. Most of the solvent was evaporated and the residue was treated overnight with aqueous potassium fluoride. The organic phase was dried and evaporated to give Z-1,2-di-(2-fluoropyridinyl)ethylene as a solid which was recrystallized from hexane/ethyl acetate (0.47 g) mp 93°-95° C.

Workup

  1. temperaturewas refluxed under argon for 4 hours
  2. customMost of the solvent was evaporated
  3. additionthe residue was treated overnight with aqueous potassium fluoride
  4. customThe organic phase was dried
  5. customevaporated

Sources & evidence

ORD record
ord-cd63bc6f420f41e1ae7737b3fa55c19d
Source dataset
uspto-grants-1999_02
Patent number
US05869482

Reaction notes

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