2-Bromopyridine → 6'-Methoxy-2,3'-bipyridyl

HRID 402591Notes

Reaction equation

HRID 402591 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11][CH:12]=1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCCC1>[CH3:14][O:13][C:10]1[N:11]=[CH:12][C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 27348955-Bromo-2-methoxypyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 108993656'-Methoxy-2,3'-bipyridyl

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
10 °C

Procedure

In a 300 mL inner volume flask replaced by nitrogen, tetrahydrofuran solution of 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) of 5-bromo-2-methoxypyridine (9.4 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 added dropwise to the tetrahydrofuran solution (20 g) containing 2-bromopyridine (7.9 g, 50.0 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (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-methoxy-3,2′-bipyridine could not be obtained.

Workup

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

Sources & evidence

ORD record
ord-0b6c20562e04427b96ff9b3df46b06ea
Source dataset
uspto-grants-2014_06
Patent number
US08742127B2

Reaction notes

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