Trifluoroacetic acid → HCID 67490868, Verbindung

HRID 1919849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919849
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:16])[CH3:2].[CH:18]1([S:24]([C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=2[CH:29]=O)(=[O:26])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH:18]1([S:24]([C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=2[CH2:29][C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=3)[N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:17])[C:7]=2[CH3:16])(=[O:25])=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 44185546Ethyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 86633019HCID 86633019, Verbindung

Produkt 1

HCID 67490868HCID 67490868, VerbindungAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of [5-fluoro-2-methyl-1H-indol-1-yl]acetic acid ethyl ester (0.85 g, 3.62 mmol) at room temperature in dichloromethane (20 mL) was added 2-(cyclohexylsulfonyl)benzaldehyde (1.00 g, 3.97 mmol) followed by triethylsilane (2.9 mL, 18.3 mmol). TFA (0.85 mL, 11.0 mmol) was then added dropwise over 15 minutes, and after the addition was complete, the resulting mixture was stirred for 2 hours. Saturated aqueous NaHCO3 was then added to the solution, and the separated organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The resulting solid was purified by trituration with light petroleum then recrystallised from an ethyl acetate/hexanes mixture to afford ethyl 2-(3-(2-(cyclohexylsulfonyl)benzyl)-5-fluoro-2-methyl-1H-indol-1-yl)acetate (0.875 g, 1.86 mmol, 51%).

Aufarbeitung

  1. additionafter the addition
  2. washthe separated organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resulting solid was purified by trituration with light petroleum
  7. customthen recrystallised from an ethyl acetate/hexanes mixture

Quellen und Nachweise

ORD-Eintrag
ord-a16ad27d8af444009b7d87c7fdbd775d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168673B2

Notizen zur Reaktion

Wird geladen…