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Ammonium Chloride → 2-(2-Ethoxycarbonylfuran-5-yl-methyl)-1-(4-fluorobenzyl)-5-methanesulfonylindole

HRID 1432273
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Reaktionsgleichung

Reaktionsgleichung von HRID 1432273
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=3)=[CH:9][CH:10]=1)=[O:5])[CH3:2].[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1.[Cl-].[NH4+]>O1CCCC1.C([N-]C(C)C)(C)C.[Li+]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][C:12]2[N:13]([CH2:30][C:29]3[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=3)[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=3)=[CH:9][CH:10]=1)=[O:5])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 680214-Fluorobenzyl bromideHCID 225044502-(2-Ethoxycarbonylfuran-5-yl-methyl)-5-methanesulfonylindole

Produkt 1

HCID 225044152-(2-Ethoxycarbonylfuran-5-yl-methyl)-1-(4-fluorobenzyl)-5-methanesulfonylindole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel
HCID 2724682Lithium diisopropylamideLösungsmittel

Versuchsvorschrift

To a solution of the compound obtained in Example 30 (5) (0.0592 g) in tetrahydrofuran (2 ml), 2.0 M lithium diisopropylamide solution (0.0852 ml) was added dropwise at −78° C. and the mixture was stirred for 30 minutes. 4-Fluorobenzyl bromide (0.02 ml) was then added to the mixture, followed by stirring at the same temperature for, 30 minutes. The reaction solution was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution, dried over anhydride magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 0.005 g of the desired product.

Aufarbeitung

  1. stirringby stirring at the same temperature for, 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous NaCl solution
  4. dry with materialdried over anhydride magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated

Quellen und Nachweise

ORD-Eintrag
ord-2021a4b6e7c14880a26b1d52a79b4aac
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612070B2

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