6-methanesulfonyl-1H-indole → (6-Methanesulfonyl-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 227425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227425
[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([Mg]Br)C.[CH3:18][C:19]1([CH3:27])[C:21]([CH3:23])([CH3:22])[CH:20]1[C:24](Cl)=[O:25]>[Cl-].[Zn+2].[Cl-]>[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:24]([CH:20]3[C:21]([CH3:23])([CH3:22])[C:19]3([CH3:27])[CH3:18])=[O:25])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 27610676-methanesulfonyl-1H-indoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 24824474(6-Methanesulfonyl-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanoneAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007855ZincchlorideKatalysator

Versuchsvorschrift

The 6-(methylsulfonyl)-1H-indole (Apollo Scientific, 1.0 g, 5.1 mmol), ethylmagnesium bromide (1.0 M solution in THF, 6.1 mL, 6.1 mmol), zinc chloride (1.0 M solution in Et2O, 6.1 mL, 6.1 mmol) and the product of Example 1A (7.7 mmol) were processed as described in Example 1B to provide the title compound (0.21 g, 0.66 mmol, 13% yield). MS (DCI/NH3) m/z 378 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-5b6d8f769b1a4f28889639640f871565
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560481B2

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