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1,1-Dichloroethane → {5-Fluoro-2-methyl-3-[2-(pyrimidine-5-sulfonyl)benzyl]indol-1-yl}acetic acid methyl ester

HRID 1944466
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1944466
[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10](Cl)=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:15].[N:17]1[CH:22]=[C:21]([S:23]([C:26]2[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=2[CH:28]=O)(=[O:25])=[O:24])[CH:20]=[N:19][CH:18]=1.ClC(Cl)C.C([SiH](CC)CC)C.[F:45]C(F)(F)C(O)=O>C(=O)([O-])O.[Na+]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:45])=[CH:11][CH:12]=2)[C:7]([CH2:28][C:27]2[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=2[S:23]([C:21]2[CH:22]=[N:17][CH:18]=[N:19][CH:20]=2)(=[O:25])=[O:24])=[C:6]1[CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 63651,1-DichloroethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 60074868Methyl 2-(5-chloro-2-methyl-1H-indol-1-yl)acetateHCID 866522002-(Pyrimidine-5-sulfonyl)benzaldehyde

Produkt 1

HCID 67044321
{5-Fluoro-2-methyl-3-[2-(pyrimidine-5-sulfonyl)benzyl]indol-1-yl}acetic acid methyl ester
Ausbeute 18,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A mixture of (5-chloro-2-methylindol-1-yl)acetic acid methyl ester (0.50 g), 2-(pyrimidine-5-sulfonyl)benzaldehyde (0.35 g) and dichloroethane (50 mL) at −70° C. was treated sequentially with triethylsilane (2.5 g) and trifluoroacetic acid (0.81 g), and the resulting mixture was stirred at −70° C. for 1 hour. The mixture was slowly warmed to room temperature and stirred at this temperature for 18 hours. The mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and the phases were separated. The organic phase was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (4:1 to 2:3 by volume) to afford the title compound as a brown oil (0.12 g).

Aufarbeitung

  1. temperatureThe mixture was slowly warmed to room temperature
  2. stirringstirred at this temperature for 18 hours
  3. customthe phases were separated
  4. concentrationThe organic phase was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting with a mixture of cyclohexane and ethyl acetate (4:1 to 2:3 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-d3e0009280754e368c8e93bcee6923e9
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394836B2

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