5'-Bromo-2,3'-bipyridine → [2,3'-Bipyridine]-5'-carbonitrile

HRID 2111682Notes

Reaction equation

HRID 2111682 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.[Br-].[N:15]1C=CC=C[C:16]=1[Zn+]>C1COCC1>[C:16]([C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1)#[N:15]

Participants

4

Reactant 2

HCID 227351815'-Bromo-2,3'-bipyridineHCID 178418723HCID 178418723, compound

Product 1

HCID 23342325[2,3'-Bipyridine]-5'-carbonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2-(3-Bromopyridin-5-yl)pyridine (2 g, 10.9 mmol) in THF (10 ml) was added dropwise to a solution of 2-pyridylzincbromide (22 ml of a 0.5M solution in THF, 11 mmol) in THF (10 ml) under a nitrogen atmosphere. Tetrakis (triphenylphosphine)palladium(0) (630 mg, 0.54 mmol) was added and the reaction stirred at ambient temperature for 18 hours. The reaction was quenched with saturated aqueous ammonium chloride solution then the volatiles were removed by evaporation. The residue was suspended in water then extracted with DCM. The organic extracts were combined, washed with water then filtered through phase separating paper and the volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with hexane:EtOAc (2:1). The purified product was triturated with diethyl ether to give the title compound (0.98 g, 50%) as a white solid. NMR (DMSO): 7.47 (t, 1H), 7.97 (t, 1H), 8.15 (d, 1H), 8.75 (d, 1H), 8.90 (d, 1H), 9.07 (s, 1H), 9.53 (s, 1H); m/z 182 (MH)+.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  2. customthe volatiles were removed by evaporation
  3. extractionthen extracted with DCM
  4. washwashed with water
  5. filtrationthen filtered through phase
  6. customseparating paper
  7. customthe volatiles removed by evaporation
  8. customThe residue was purified by column chromatography on silica gel eluting with hexane:EtOAc (2:1)
  9. customThe purified product was triturated with diethyl ether

Sources & evidence

ORD record
ord-9679292fce72441ba086b7dfca8a1ff1
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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