5,6-Bis(phenylmethoxy)-1H-indole → (5,6-Bis-benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 227428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227428
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Br)C.[CH3:30][C:31]1([CH3:39])[C:33]([CH3:35])([CH3:34])[CH:32]1[C:36](Cl)=[O:37]>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:14][CH:13]=[C:12]2[C:36]([CH:32]1[C:33]([CH3:35])([CH3:34])[C:31]1([CH3:39])[CH3:30])=[O:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 209205,6-Bis(phenylmethoxy)-1H-indoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 67269830(5,6-Bis-benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanoneAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The 5,6-dibenzyloxyindole (Sigma, 0.60 g, 1.8 mmol), ethylmagnesium bromide (1.0 M solution in THF, 2.2 mL, 2.2 mmol), zinc chloride (1.0 M solution in Et2O, 2.2 mL, 2.2 mmol) and the product of Example 1A (2.7 mmol) in 20 mL of dichloromethane were processed as described in Example 1B to provide the title compound (0.45 g, 0.99 mmol, 55% yield). MS (DCI/NH3) m/z 454 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-4ad9650b0f224fbe8fc495790ce41221
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560481B2

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