Tetrabutylammonium Fluoride → 5-Fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 2108739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108739
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:21]=[C:22]2[CH:28]=[CH:27][N:26]([Si](C(C)C)(C(C)C)C(C)C)[C:23]2=[N:24][CH:25]=1>C1COCC1>[F:19][C:20]1[CH:21]=[C:22]2[CH:28]=[CH:27][NH:26][C:23]2=[N:24][CH:25]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 242292265-Fluoro-1-[tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 207844625-Fluoro-1H-pyrrolo[2,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Tetrabutylamonium fluoride, 1M in THF (2 mL), was added to a stirred solution of 5-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1 g, 3.94 mmol) in THF (10 mL) at room temperature and stirred for 15 min. The solvent was evaporated and the crude product was purified by Biotage HPFC system (40-75% EtOAc/Hexane) to afford 5-fluoro-1H-pyrrolo[2,3-b]pyridine as a white solid (0.45 g, 84); Mass Spec.; MS 137 (M+1); 1H NMR(DMSO-d6, 500 MHz) δ 11.75(s, 1H), 8.17(t,1H), 7.81(dd,1H), 7.55(t,1H), 6.44(dd,1H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe crude product was purified by Biotage HPFC system (40-75% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fb6d70854c7547e5a9b8229033fd6e68
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514448B2

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