Sodium Carbonate → 5-Phenylpyridine-2-carbonitrile

HRID 1177970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177970
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.O.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>[C:16]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 38339425-Chloro-2-cyanopyridine

Produkt 1

HCID 9352765-Phenylpyridine-2-carbonitrileAusbeute 24,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 22272177Toluene waterLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-chloro-2-cyanopyridine (300 mg, 2.17 mmol) in toluene: H2O (7:3) (10 mL) was added Na2CO3 (459 mg, 4.33 mmol) followed by Pd(PPh3)4 (500 mg, 0.43 mmol) and phenylboronic acid (337 mg, 2.60 mmol) at room temperature. The resulting mixture was heated to reflux for 3 hrs. The reaction mixture was then diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over sodium sulphate and concentrated. The resulting residue was purified by column chromatography (using silica gel 60-120 mesh and 4% ethylacetate in hexane as eluent) to afford 96 mg (24.6% yield) of 5-phenyl-pyridine-2-carbonitrile. LCMS Purity: 97.5%

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 hrs
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography (using silica gel 60-120 mesh and 4% ethylacetate in hexane as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-87b6253c06fa4ea582ce740af1913552
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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