Sodium Carbonate → Methyl 3-chloro-6'-methyl[2,3'-bipyridine]-5-carboxylate

HRID 2089115Notes

Reaction equation

HRID 2089115 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.[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24]([Cl:26])[C:23](Cl)=[N:22][CH:21]=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>[CH3:17][O:18][C:19]([C:20]1[CH:25]=[C:24]([Cl:26])[C:23]([C:11]2[CH:12]=[N:13][C:8]([CH3:7])=[CH:9][CH:10]=2)=[N:22][CH:21]=1)=[O:28]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27630812-Methylpyridine-5-boronic acidHCID 2782166Methyl 5,6-Dichloronicotinate

Product 1

HCID 57825687Methyl 3-chloro-6'-methyl[2,3'-bipyridine]-5-carboxylateYield 888.2%

Reagents, catalysts & solvents 3

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

Procedure

0.29 of Na2CO3 (0.273 mmol), 0.25 g of 6-methylpyridin-3-ylboronic acid (11) (0.18 mmol) and 0.11 g of Pd(PPh3)4 were added to 0.4 g of 5,6-dichloro-nicotinic acid methyl ester (10) (0.2 mmol) prepared in Example 7 dissolved in 14 mL of 1,2-dimethoxyethane and 7 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: chloroform/methanol=10/1) to obtain 0.42 g of 3-chloro-6′-methyl-[2,3′]bipyridyl-5-carboxylic acid methyl ester (yield 88%).

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: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-eda2691ea4aa42608c2f49971c2ff034
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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