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

HRID 402587Notes

Reaction equation

HRID 402587 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[N:11][CH:12]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>O1CCCC1>[Cl:13][C:10]1[N:11]=[CH:12][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 27344145-Bromo-2-chloropyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 109543616'-Chloro-[2,3']bipyridinyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
10 °C

Procedure

In a 300 mL inner volume flask replaced by nitrogen, tetrahydrofuran solution containing isopropylmagnesium chloride (19.5% by weight, 30.3 g, 57.5 mmol) was charged, and cooled at 10° C., and then, tetrahydrofuran solution (20 g) containing 5-bromo-2-chloropyridine (9.6 g, 50.0 mmol) was added dropwise in the range of 10 to 20° C. for 1.0 hour. After adding dropwise, the reaction mixture was stirred in the range of 10 to 20° C. for 1.5 hours, and then reaction mixture was added dropwise to the solution of tetrahydrofuran (20 g) containing 2-bromopyridine (7.9 g, 50.0 mmol) and [1,1′-bis(diphenylphosphino)propane]nickel dichloride (0.14 g, 0.25 mmol) in the range of 10 to 20° C. for 2.0 hours. After adding dropwise, the reaction mixture was stirred in the range of 10 to 20° C. for 4.0 hours. However, 6-chloro-3,2′-bipyridine could not be obtained.

Workup

  1. additionwas charged
  2. additionwas added dropwise in the range of 10 to 20° C. for 1.0 hour
  3. additionAfter adding dropwise
  4. customreaction mixture
  5. additionAfter adding dropwise
  6. stirringthe reaction mixture was stirred in the range of 10 to 20° C. for 4.0 hours

Sources & evidence

ORD record
ord-1cfe993f7d844f3e89382f29e877cee1
Source dataset
uspto-grants-2014_06
Patent number
US08742127B2

Reaction notes

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