Trimethylsilylacetylene → 5-Fluoro-2-((trimethylsilyl)ethynyl)pyridin-3-amine

HRID 2409036

Reaktionsgleichung

Reaktionsgleichung von HRID 2409036
Br[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:9][C:5]1[CH:6]=[C:7]([NH2:8])[C:2]([C:15]#[C:14][Si:11]([CH3:13])([CH3:12])[CH3:10])=[N:3][CH:4]=1

Komponenten

5

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 404273672-Bromo-5-fluoropyridin-3-amine

Produkt 1

HCID 866898515-Fluoro-2-((trimethylsilyl)ethynyl)pyridin-3-amineAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 2-bromo-5-fluoropyridin-3-amine (3.3 g, 17.3 mmol), TEA (7.3 mL, 51.9 mmol), PdCl2(PPh3)2 (1.2 g, 1.73 mmol), and Cu(I)I (0.33 g, 1.73 mmol) in THF (50 mL) at 0° C. under nitrogen was added a solution of (trimethylsilyl)acetylene (3.39 mL, 34.6 mmol). The mixture was stirred at RT for 2 h and then concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (5:1) to afford 2.0 g (915) of 5-fluoro-2-((trimethylsilyl)ethynyl)pyridin-3-amine as a yellow solid. MS (ESI): m/z=209.1 [M+1]+.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by SiO2 chromatography
  3. washeluting with petroleum ether/EtOAc (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-4035b68c98084901a958e68b87aef528
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815877B2

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