Water → 3-Chloro-6'-methyl-2,3'-bipyridine

HRID 1497488Notes

Reaction equation

HRID 1497488 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.O.C([O-])([O-])=O.[Na+].[Na+].[CH3:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][N:18]=1>COCCOC.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:8][C:7]1[C:2]([C:20]2[CH:19]=[N:18][C:17]([CH3:16])=[CH:22][CH:21]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 169882,3-DichloropyridineHCID 27630812-Methylpyridine-5-boronic acid

Product 1

HCID 596732853-Chloro-6'-methyl-2,3'-bipyridineYield 91.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 0.5 g (3.6 mmol) 2,3-dichloropyridine in 20 mL 1,2-dimethoxyethane and 20 mL distilled water were added 2.2 g (21.1 mmol) Na2CO3, 0.41 g (3.0 mmol) 2-methylpyridine-5-boronic acid and 50 mg Pd(PPh3)4, followed by stirring for 18 hours in a heat flux condition. After being cooled to room temperature, the solution was 50% concentrated in a vacuum condition. The aqueous layer was washed with ethyl acetate. Thereafter, the organic layer was dried over magnesium sulfate and vacuum concentrated. The concentrate was separated using column chromatography (developing solvent: ethyl acetate/hexane=1/10) to produce 0.56 g of 3-chloro-2-(6-methylpyridin-3-yl)pyridine (yield 80%).

Workup

  1. concentrationconcentrated in a vacuum condition
  2. washThe aqueous layer was washed with ethyl acetate
  3. dry with materialThereafter, the organic layer was dried over magnesium sulfate and vacuum
  4. concentrationconcentrated
  5. customThe concentrate was separated

Sources & evidence

ORD record
ord-0fc4b277fe5b4f57a6c63b10c3fc6a60
Source dataset
uspto-grants-2015_12
Patent number
US09199965B2

Reaction notes

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