Potassium Carbonate → 5-Methyl-2-phenylpyridine

HRID 736379

Reaktionsgleichung

Reaktionsgleichung von HRID 736379
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+]>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.CC#N>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:12][CH:13]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 5642162-Bromo-5-methylpyridine

Produkt 1

HCID 474675-Methyl-2-phenylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Phenylboronic acid (732 mg, 6 mmol), 2-bromo-5-methylpyridine (1.03 g, 5.99 mmol), and Pd (PPh3)4 (350 mg, 0.303 mmol) were heated in 0.4 M K2CO3 (30 mL, 12 mmol) and CH3CN (30 mL) at 90° overnight. The mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between brine and ethyl acetate. The organic layer was separated, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (9:1 hexanes:ethyl acetate) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.50 (m, 1H), 8.05 (m, 2H), 7.85 (d, J=8.4 Hz, 1H), 7.68-7.71 (m, 1H), 7.37-7.50 (m, 3H), 2.34 (s, 3H); MS (APCI+) m/z 170 (M+H)+.

Aufarbeitung

  1. customat 90°
  2. customovernight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between brine and ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (9:1 hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9e7489330df747f0a94e6c7b2828f6bb
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595332B2

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