Methyl indole-6-carboxylate → 3-(2,2,3,3-Tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carboxylic Acid Methyl Ester

HRID 227412

Reaktionsgleichung

Reaktionsgleichung von HRID 227412
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].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-]>[CH3:1][O:2][C:3]([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]

Komponenten

6

Edukt 3

HCID 639844Methyl indole-6-carboxylateHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 248239313-(2,2,3,3-Tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carboxylic Acid Methyl EsterAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of methyl-indole-6-carboxylate (2.0 g, 11.4 mmol), ethylmagnesium bromide (1.0 M solution in THF, 14 mL, 14 mmol), zinc chloride (1.0 M solution in Et2O, 14 mL, 14 mmol) and the product of Example 1A (17 mmol) in 30 mL of dichloromethane was processed as described in Example 1B to provide the title compound (1.35 g, 4.5 mmol, 40% yield). MS (DCI/NH3) m/z 300 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-845082f05d9a4e1696ef1f36e0648b77
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560481B2

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