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Carbon tetrabromide → 5-Bromo-4-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

HRID 79592
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 79592
[Li]C(CC)C.[F:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[N:13]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:15][C:8]=12.C(Br)(Br)(Br)[Br:27].[Cl-].[NH4+]>C1COCC1>[Br:27][C:12]1[C:7]([F:6])=[C:8]2[CH:15]=[CH:14][N:13]([Si:16]([CH:20]([CH3:22])[CH3:21])([CH:23]([CH3:25])[CH3:24])[CH:17]([CH3:18])[CH3:19])[C:9]2=[N:10][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11205Carbon tetrabromideHCID 25517Ammonium ChlorideHCID 112663344-Fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineHCID 178418400CID 53628100

Produkt 1

HCID 497589465-Bromo-4-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

s-BuLi (53.7 mL, 75.2 mmol, 1.4M in cyclohexane) was added to a solution of 4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (10.0 g, 34.2 mmol, prepared as described in L′Heureux, et al. Org. Lett., 5(26), p. 5023 (2003)) in THF (250 mL) at −78° C., and the reaction was stirred at −78° C. for 30 minutes. A solution of CBr4 (28.3 g, 85.5 mmol) in THF (40 mL) was added next, and the reaction was stirred at this temperature for 1 hour. A saturated ammonium chloride solution (80 mL) was then added, and the reaction was extracted with hexane (200 mL), washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was then purified by column chromatography (hexane) to give 5-bromo-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (7.8 g, 61.4% yield).

Aufarbeitung

  1. stirringthe reaction was stirred at this temperature for 1 hour
  2. extractionthe reaction was extracted with hexane (200 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was then purified by column chromatography (hexane)

Quellen und Nachweise

ORD-Eintrag
ord-25abc313e1fa458f8fb98bc6e8fd2248
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08841304B2

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