Sodium Carbonate → 3-Chloro-6'-methyl-5-vinyl-2,3'-bipyridine

HRID 2089117Notes

Reaction equation

HRID 2089117 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH3:7][C:8]1[N:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.Cl[C:18]1[C:23]([Cl:24])=[CH:22][C:21]([CH:25]=[CH2:26])=[CH:20][N:19]=1>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:24][C:23]1[C:18]([C:11]2[CH:12]=[N:13][C:8]([CH3:7])=[CH:9][CH:10]=2)=[N:19][CH:20]=[C:21]([CH:25]=[CH2:26])[CH:22]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27630812-Methylpyridine-5-boronic acidHCID 574168492,3-Dichloro-5-ethenylpyridine

Product 1

HCID 578257023-Chloro-6'-methyl-5-vinyl-2,3'-bipyridineYield 90.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

8.1 g of Na2CO3 (76 mmol), 3.5 g of 6-methylpyridin-3-ylboronic acid (11) (25 mmol), and 0.97 g of Pd(PPh3)4 were added to 4.9 g of compound (8) (28 mmol) prepared in Example 5 dissolved in 100 mL of 1,2-dimethoxyethane and 100 mL of distilled water, and refluxed under heating and stirring for 18 hours. The mixture was cooled to room temperature, and concentrated about 50% under reduced pressure. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate, concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: ethyl acetate/hexane=1/4) to obtain 5.2 g of 3-chloro-6′-methyl-5-vinyl-2,3′-bipyridine (yield 90%).

Workup

  1. temperatureunder heating
  2. concentrationconcentrated about 50% under reduced pressure
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated by column chromatography (eluting solvent: ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-aaa86aa84ba34548a512998a89ef3ead
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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