Sodium Carbonate → 2-Fluoro-3-{3-[(trimethylsilyl)ethynyl]phenyl}pyridine

HRID 2220444

Reaktionsgleichung

Reaktionsgleichung von HRID 2220444
Br[C:2]1[CH:3]=[C:4]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[F:14][C:15]1[C:20](B(O)O)=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[F:14][C:15]1[C:20]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=2)=[CH:19][CH:18]=[CH:17][N:16]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 3683324((3-Bromophenyl)ethynyl)trimethylsilane

Produkt 1

HCID 687015872-Fluoro-3-{3-[(trimethylsilyl)ethynyl]phenyl}pyridineAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of [(3-bromophenyl)ethynyl](trimethyl)silane (2.28 g, 9.0 mmol) in DME (150 mL) is added (2-fluoropyridin-3-yl)boronic acid (1.41 g, 10.0 mmol), tetrakis(triphenylphosphine)palladium (0.52 g, 0.5 mmol) and a solution of sodium carbonate (3.8 g, 36.0 mmol) in H2O (15 mL) at room temperature. After refluxing for 3 h, the reaction mixture is cooled, quenched with saturated sodium carbonate, diluted with EtOAc. The two layers are separated and the aqueous layer is extracted with EtOAc. The combined organic extracts are washed with brine, dried (MgSO4) and concentrated. The crude mixture is purified by chromatography (silica gel, EtOAc/hexane: 5/95) to give the 2-fluoro-3-{3-[(trimethylsilyl)ethynyl]phenyl}pyridine (2.25 g, 91%) as an oil. MS(+) APPI: 270 (M+H)+.

Aufarbeitung

  1. customat room temperature
  2. temperatureAfter refluxing for 3 h
  3. temperaturethe reaction mixture is cooled
  4. customquenched with saturated sodium carbonate
  5. additiondiluted with EtOAc
  6. customThe two layers are separated
  7. extractionthe aqueous layer is extracted with EtOAc
  8. washThe combined organic extracts are washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customThe crude mixture is purified by chromatography (silica gel, EtOAc/hexane: 5/95)

Quellen und Nachweise

ORD-Eintrag
ord-a21f3320252e4dfdb49b4eeb051f8169
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417047B2

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