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Potassium Carbonate → 6-(4-Methoxyphenyl)-2-pyridinecarbonitrile

HRID 499458
Notes
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Reaction equation

HRID 499458 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](OB(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.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.O.C(OCC)(=O)C>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 1184246-Chloropyridine-2-carbonitrileHCID 147699944-Methoxyphenyl boric acid

Product 1

HCID 229396246-(4-Methoxyphenyl)-2-pyridinecarbonitrileYield 89.4%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent2×
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-2-pyridinecarbonitrile (0.70 g, 5.0 mmol) and 4-methoxyphenylboric acid (1.17 g, 7.7 mmol) were dissolved in toluene (60 ml)-ethanol (15 ml), and potassium carbonate (1.75 g, 12.6 mmol) and water (15 ml) were added thereto. The mixture was deairated under reduced pressure for 10 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.29 g, 0.25 mmol) was added to the reaction mixture under argon atmosphere, and the mixture was refluxed for 16 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (4:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (0.94 g, 88%).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 16 hrs
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. washThe fractions eluted with hexane-ethyl acetate (4:1
  7. customv/v) were collected
  8. concentrationconcentrated
  9. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-0645fc9362f64f5db395b680ed297e74
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767665B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes