Dichloromethane → ethyl 2-(7-acetamido-4-fluoro-1H-indol-3-yl)-2-oxoacetate

HRID 2097670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2097670
[F:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]2[C:3]=1C=C[NH:6]2.[Al+3].[Cl-].[Cl-].[Cl-].Cl[C:20]([C:22]([CH2:24][CH3:25])=[O:23])=[O:21].[C:26]([O-:29])(O)=O.[Na+].[CH2:31](Cl)Cl>>[C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]2[C:7]=1[NH:6][CH:25]=[C:24]2[C:22](=[O:23])[C:20]([O:29][CH2:26][CH3:31])=[O:21])(=[O:14])[CH3:13]

Komponenten

6

Edukt 5

HCID 6344Dichloromethane2×HCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride2×HCID 11007880Butanoyl chloride, 2-oxo-HCID 66728479N-(4-Fluoro-1H-indol-7-yl)acetamide

Produkt 1

HCID 66728362ethyl 2-(7-acetamido-4-fluoro-1H-indol-3-yl)-2-oxoacetate

Versuchsvorschrift

N-(4-fluoro-1H-indol-7-yl)acetamide (1 eq.) was added to a suspension of AlCl3 (1 eq.) in CH2Cl2 (100 ml). After 15 min, a premixed suspension of AlCl3 (2 eq.) and ClCOCOEt (2 eq.) in CH2Cl2 was added and stirring was continued at room temperature for 1 hour before iced saturated NaHCO3 solution was added. The aqueous phase was extracted with EtOAc. The combined organic layer was dried over MgSO4. After filtration and concentration, the crude product was purified by silica gel column chromatography to afford ethyl 2-(7-acetamido-4-fluoro-1H-indol-3-yl)-2-oxoacetate. MS m/z: (M+H)+ calc'd for C14H14FN2O4:293.09. Found 293.11. HPLC retention time: 0.98 minutes (column E, solvent system II). 1H NMR (300 MHz, CD3OD) 8.32 (s, 1H), 7.16 (m, 1H), 6.94 (m, 1H), 4.43 (q, 2H, J=7.2 Hz), 2.24 (s, 3H), 1.39 (t, 3H, J=7.2 Hz).

Aufarbeitung

  1. additionwas added
  2. additionwas added
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bf2e4f71ba1f4212a447961092e16718
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450361B2

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