6-(Trifluoromethyl)indole → (2,2,3,3-Tetramethyl-cyclopropyl)-(6-trifluoromethyl-1H-indol-3-yl)methanone

HRID 227427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227427
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.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]>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH3:18][C:19]1([CH3:27])[C:21]([CH3:23])([CH3:22])[CH:20]1[C:24]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([C:2]([F:1])([F:12])[F:13])=[CH:4][CH:5]=2)[NH:9][CH:8]=1)=[O:25]

Komponenten

6

Edukt 3

HCID 27775236-(Trifluoromethyl)indoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 24824344(2,2,3,3-Tetramethyl-cyclopropyl)-(6-trifluoromethyl-1H-indol-3-yl)methanoneAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 6-(trifluoromethyl)indole (Lancaster, 1.0 g, 5.4 mmol), ethylmagnesium bromide (1.0 M solution in THF, 6.6 mL, 6.6 mmol), zinc chloride (1.0 M solution in Et2O, 6.6 mL, 6.6 mmol) and the product of Example 1A (8.1 mmol) in 40 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.17 g, 0.53 mmol, 10% yield). MS (DCI/NH3) m/z 310 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-fc333d56959146c39e38e0df07e10780
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560481B2

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