Tetrabutylammonium Fluoride → Bpr-0L075

HRID 710324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710324
[Si]([C:8]1[N:9](C(=O)C)[C:10]2[C:15]([C:16]=1[C:17](=[O:30])[C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=1)=[CH:14][CH:13]=[C:12]([O:31][CH3:32])[CH:11]=2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:32][O:31][C:12]1[CH:11]=[C:10]2[C:15]([C:16]([C:17]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)=[O:30])=[CH:8][NH:9]2)=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 667265851-(2-(tert-Butyldimethylsilyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)ethanone

Produkt 1

HCID 10359957Bpr-0L075Ausbeute 108,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of the product of Step A (0.52 g, 1.05 mmol) and 1M TBAF in THF (1 ml) in THF (10 ml) was refluxed for 2 h. The solvent was evaporated and the residue was taken in EtOAc, washed with 1M HCl and organic layer was passed through silica gel bead. The solvent was evaporated and the residue was crystallized from MeOH to give the desired product (0.39 g; 100%), as creamy solid. 1H-NMR (CDCl3) 3.83 (s, 3H); 3.87 (s, 3H); 3.91 (s, 3H); 6.93-6.96 (m, 2H); 7.06 (s, 2H); 7.62 (s, 1H); 8.22 (d, 1H, J=9.36 Hz); 9.24 (broad s, 1H).

Aufarbeitung

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was evaporated
  3. washwashed with 1M HCl and organic layer
  4. customThe solvent was evaporated
  5. customthe residue was crystallized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-6433c02f67ba429f87cf496d8a538c65
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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