Triphenylphosphine → 5'-Bromo-2,3'-bipyridine

HRID 50571Notes

Reaction equation

HRID 50571 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Zn+]>C1COCC1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 693693,5-DibromopyridineHCID 178479831HCID 178479831, compound

Product 1

HCID 227351815'-Bromo-2,3'-bipyridine

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,5-dibromopyridine (2.5 g, 10.5 mmol), PPh3 (210 mg, 0.8 mmol) in degassed THF (2 mL) was treated with Pd2(dba)3 (Tris(dibenzylideneacetone)dipalladium (0), 91.5 mg, 0.1 mmol) at 25° C. under N2. A solution of 2-pyridinyl zinc chloride (21 mL, 0.5 M in THF, Aldrich) in THF was added and the resulting solution was warmed to reflux for 16 h. The solution was allowed to cool to room temperature, diluted with EtOAc (200 mL), washed with water (2×100 mL), dried (MgSO4), filtered and was concentrated in vacuo. Purification by flash chromatography (EtOAc) afforded the title compound as a white solid. MS 236 (M+H)+.

Workup

  1. temperaturethe resulting solution was warmed
  2. temperatureto reflux for 16 h
  3. washwashed with water (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationwas concentrated in vacuo
  7. customPurification by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-a28cba4d344a4cdb91c299195a232b19
Source dataset
uspto-grants-2004_03
Patent number
US06713455B2

Reaction notes

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