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Trifluoroacetic acid → [5-Fluoro-2-methyl-3-(2-sulfobenzyl)indol-1-yl]acetic acid methyl ester

HRID 1944425
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1944425
[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:15].[Na+].[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([O-:29])(=[O:28])=[O:27])=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:18][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[S:26]([OH:29])(=[O:28])=[O:27])=[C:6]1[CH3:15]
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Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 3794540Sodium o-formylbenzenesulfonateHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetate

Produkt 1

HCID 86652190[5-Fluoro-2-methyl-3-(2-sulfobenzyl)indol-1-yl]acetic acid methyl esterAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

A mixture of (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (1.0 g), 2-formylbenzensulfonic acid sodium salt (0.94 g) and 1,2-dichloroethane (15 mL) at 0° C. was treated dropwise with a mixture of triethylsilane (4.3 mL), trifluoroacetic acid (1.0 mL) and 1,2-dichloroethane (10 mL), and the resulting mixture was stirred at room temperature for 6 hours. The mixture was extracted with ethyl acetate and the combined organic extract was dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of methanol and dichloromethane (0:1 to 1:9 by volume) to afford the title compound as a purple gum (1.3 g).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. extractionthe combined organic extract
  3. dry with materialwas dried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of methanol and dichloromethane (0:1 to 1:9 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-e70b1af3948540bb810480d9cc1aec39
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394836B2

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