Potassium Carbonate → 4-(4-Pyridinyl)-6-quinolinecarbonitrile

HRID 1952301Notes

Reaction equation

HRID 1952301 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[N:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 204935814-Chloroquinoline-6-carbonitrile

Product 1

HCID 667820474-(4-Pyridinyl)-6-quinolinecarbonitrileYield 95.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-6-quinolinecarbonitrile (8.7 g, 46.2 mmol), 4-pyridineboronic acid (8.52 g, 69.3 mmol), tetrakis(triphenylphosphine)palladium(0) (2.67 g, 2.31 mmol) and 2 M potassium carbonate (69.3 mL, 3 eq) in 1,4-dioxane (380 mL) is heated at reflux for 3.5 hours. The dioxane is evaporated and the crude product purified by silica gel chromatography eluting with methylene chloride/methanol 0-4%. A yield of 10.23 g (95%) of the title compounds was obtained.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3.5 hours
  3. customThe dioxane is evaporated
  4. customthe crude product purified by silica gel chromatography
  5. washeluting with methylene chloride/methanol 0-4%

Sources & evidence

ORD record
ord-3e2e915f07904477a81fbf9d76c51c2b
Source dataset
uspto-grants-2013_03
Patent number
US08404837B2

Reaction notes

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