Ethyl Acetate → Ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylate

HRID 131641

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Cl.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([F:16])[CH:18]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A suspension of 0.207 g (1 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 0.173 g (1.2 mmol) of 3-fluorobenzyl chloride and 0.276 g (2 mmol) of potassium carbonate in 10 ml of dimethylformamide is stirred at 60° C. for 24 hours. The reaction mixture is subsequently cooled and is poured into a mixture of ice-cold water and of ethyl acetate. After settling, the organic phase is separated and then it is washed with two times 50 ml of water and then with 50 ml of a saturated sodium chloride solution. The solution is dried over magnesium sulfate and is filtered, and then the filtrate is concentrated under reduced pressure. 0.195 g of an oil is obtained, which oil is used as is in the following stage.

Aufarbeitung

temperatureThe reaction mixture is subsequently cooled
customthe organic phase is separated
washit is washed with two times 50 ml of water
dry with materialThe solution is dried over magnesium sulfate
filtrationis filtered
concentrationthe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-276fbec6c06f45fea6c86055a2670eef
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07384969B2

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