Sodium Carbonate → 5-Chloro-2-phenyl-isonicotinonitrile

HRID 2213069Notes

Reaction equation

HRID 2213069 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[CH:12]=[C:13]([C:16]([Cl:19])=[CH:17][N:18]=1)[C:14]#[N:15].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C>[Cl:19][C:16]1[C:13]([C:14]#[N:15])=[CH:12][C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:18][CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 135602102,5-Dichloropyridine-4-carbonitrile

Product 1

HCID 219565045-Chloro-2-phenyl-isonicotinonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Tetralds(triphenylphosphine)palladium(0) (167 mg, 0.14 mmol) was added to a stirred solution of phenylboronic acid (423 mg, 3.47 mmol), 2,5-dichloro-isonicotinonitrile (550 mg, 2.89 mmol) and sodium carbonate (3.5 mL of 2M aqueous solution) in dimethoxyethane (7 mL) and ethanol (3.5 mL). The resulting suspension was stirred at reflux for 3 hours, concentrated in vacuo and water (25 mL) added. The aqueous solution was extracted with ethyl acetate (×3) and the combined organic extracts were washed with brine, dried and concentrated. Purification by column chromatography using 2% v/v ethyl acetate in hexane as eluent afforded the title compound as a solid.

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationconcentrated in vacuo and water (25 mL)
  3. additionadded
  4. extractionThe aqueous solution was extracted with ethyl acetate (×3)
  5. washthe combined organic extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-e4491911e32f4560adab8085a46aa071
Source dataset
uspto-grants-2006_09
Patent number
US07105532B2

Reaction notes

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