5-(Trifluoromethyl)-3-((trimethylsilyl)ethynyl)-pyridin-2-amine → 5-Trifluoromethyl-1H-Pyrrolo[2,3-B]Pyridine

HRID 1515911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515911
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:10]#[C:11][Si](C)(C)C)[C:6]([NH2:9])=[N:7][CH:8]=1>CN1CCCC1=O.[Cu]I>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]2[CH:10]=[CH:11][NH:9][C:6]2=[N:7][CH:8]=1

Komponenten

4

Edukt 1

HCID 467368715-(Trifluoromethyl)-3-((trimethylsilyl)ethynyl)-pyridin-2-amine

Produkt 1

HCID 307721175-Trifluoromethyl-1H-Pyrrolo[2,3-B]PyridineAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

5-Trifluoromethyl-3-trimethylsilanylethynyl-pyridin-2-ylamine (43.8 g, 170 mmol) and copper(I) iodide (6.5 g, 34 mmol) were dissolved in N-methylpyrrolidone (0.85 L). The mixture was stirred at 190° C. for 30 min. The mixture was evaporated to remove N-methylpyrrolidone in vacuo. The residue was purified by flash column chromatography (QingDao silical gel, 200-300 mesh, 40% ethyl acetate/hexanes) to afford 5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (7.5 g, 24%) as a yellow solid: LC/MS m/e calcd for C8H5F3N2 [M+H]+ 187.14, observed 187.0.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customto remove N-methylpyrrolidone in vacuo
  3. customThe residue was purified by flash column chromatography (QingDao silical gel, 200-300 mesh, 40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9d5065a2826d4c28b1cb2aaf175463c2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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