Tetrahydrofuran → HCID 21254081, Verbindung

HRID 1531538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531538
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[BrH:36].[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([Br:36])=[C:12]2[CH2:18][CH2:19][N:20]1[C:21](=[O:30])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 1548084HCID 1548084, VerbindungHCID 21226041Pyridinium hydrobromide

Produkt 1

HCID 21254081HCID 21254081, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-[2-(5-benzyloxy-1H-indol-3-yl)ethyl]isoindole-1,3-dione (800 mg in a mixture of dry 25 mL tetrahydrofuran and 25 mL dry chloroform) at 0° C. was added pyridinium hydrobromide perbromide (666 mg) and the mixture stirred at 0° C. After 23 minutes the reaction was quenched by the addition of saturated sodium bicarbonate and extracted with ethyl acetate. The organic portion was washed with saturated sodium bicarbonate (3×) and 0.3M sodium bisulfate (3×) then dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 7:2) followed by repurification by flash chromatography on silica gel (methylene chloride) gave the title compound (632 mg).

Aufarbeitung

  1. customAfter 23 minutes the reaction was quenched by the addition of saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe organic portion was washed with saturated sodium bicarbonate (3×) and 0.3M sodium bisulfate (3×)
  4. dry with materialthen dried over magnesium sulfate
  5. customPurification of the
  6. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 7:2)
  7. customfollowed by repurification by flash chromatography on silica gel (methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-b8f0a2d772c54f85aada79db713843b2
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06197975B1

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