2-Bromopyridine → 6'-Chloro-[2,3']bipyridinyl

HRID 402589Notes

Reaction equation

HRID 402589 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]1[N:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.COCCOC>[Cl:33][C:34]1[N:39]=[CH:38][C:37]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:36][CH:35]=1

Participants

9

Reactant 4

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 38450342-Chloropyridine-5-boronic acid

Product 1

HCID 109543616'-Chloro-[2,3']bipyridinylYield 87%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-bromopyridine (7.0 g, 44.0 mmol), palladium acetate (0.5 g, 2.2 mmol), triphenylphosphine (2.5 g, 9.5 mmol), potassium carbonate (37.0 g, 267.0 mmol), 1,2-dimethoxyethane (60 g) and water (80 g) were added to the resultant 6-chloro-3-pyridyl boronic acid (6.9 g, 44.0 mmol), and the reaction mixture was stirred, and then refluxed with heating for 6.0 hours. Reaction solution was cooled, and then ethyl acetate (50 g) was added, the reaction solution was stirred for 1.0 hour, and was left to stand to separate organic layer. Organic layer was washed with 10% by weight of aqueous solution of ammonium chloride (20 g), 10% aqueous solution of ammonia (20 g), 10% aqueous solution of sodium chloride (20 g), and then condensed under reduced pressure to obtain 6-chloro-3,2′-bipyridine (7.0 g, 38.3 mmol).

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 6.0 hours
  3. customReaction solution
  4. temperaturewas cooled
  5. stirringthe reaction solution was stirred for 1.0 hour
  6. waitwas left
  7. customto separate organic layer
  8. washOrganic layer was washed with 10% by weight of aqueous solution of ammonium chloride (20 g), 10% aqueous solution of ammonia (20 g), 10% aqueous solution of sodium chloride (20 g)
  9. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-bdb841b68b54432db27083dbb602d2c3
Source dataset
uspto-grants-2014_06
Patent number
US08742127B2

Reaction notes

Loading…