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

HRID 249802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249802
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 242292415-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 5-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (5, 1.40 g, 4.53 mmol) in tetrahydrofuran (15 mL) was added tetra-n-butylammonium fluoride (1.42 g, 5.43 mmol). The reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture was concentrated and isolated by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give the compound (6, 0.40 g. 58% over 2 steps). MS (ESI)[M−H+]−=153.1.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customisolated by silica gel column chromatography
  3. washeluting with 30% ethyl acetate in hexane
  4. customto give the compound (6, 0.40 g. 58% over 2 steps)

Quellen und Nachweise

ORD-Eintrag
ord-11e5a0ab5d7c4f67b4fd8368160e50a5
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863289B2

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