Tetrabutylammonium Fluoride → HCID 10250607, Verbindung

HRID 1178434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178434
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][CH2:29][N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH:32]([NH:40][C:41]([C:43]2[NH:47][C:46]3[S:48][C:49]([Cl:51])=[CH:50][C:45]=3[CH:44]=2)=[O:42])[C:31]1=[O:52])(C(C)(C)C)(C)C>C1COCC1>[Cl:51][C:49]1[S:48][C:46]2[NH:47][C:43]([C:41]([NH:40][CH:32]3[CH2:33][C:34]4[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:30]([CH2:29][CH2:28][CH2:27][OH:26])[C:31]3=[O:52])=[O:42])=[CH:44][C:45]=2[CH:50]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 21906851N-[1-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

Produkt 1

HCID 10250607HCID 10250607, VerbindungAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

TBAF (1.0 M in THF, 4.92 mL, 4.92 mmol) was added to N-[1-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 20, 1.84 g, 3.56 mmol) in THF (15 mL) and the reaction was stirred for 48 hours. The reaction was quenched by the addition of EtOAc (50 mL) and NH4Cl (aq.) (20 mL) and the organic layer was dried (MgSO4), filtered and evaporated. Purification by column chromatography afforded the title compound (1.24 g, 3.08 mmol, 86%) as a white solid.

Aufarbeitung

  1. customThe reaction was quenched by the addition of EtOAc (50 mL) and NH4Cl (aq.) (20 mL)
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-03a36a4ef2e843fdaa96ef02130f47f7
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276517B2

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