Sodium hydride → HCID 76850770, Verbindung

HRID 1683991

Reaktionsgleichung

Reaktionsgleichung von HRID 1683991
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([O:16][CH3:17])=[O:15].[H-].[Na+].Cl[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][CH:23]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][CH:23]=1)[C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([O:16][CH3:17])=[O:15]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 701281-(Chloromethyl)-4-(methylthio)benzeneHCID 82067methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

Produkt 1

HCID 76850770HCID 76850770, VerbindungAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To the indole of Example 7, Step 1, (1.00 g, 4.29 mmol) in DMF (15.0 mL) at 0° C. were added NaH 60% in oil (188 mg, 4.72 mmol) and a solution of 4-chloromethylthioanisole (810 mg, 4.7 mmol) in DMF (5.0 mL). After a period of 5 min at r.t., the reaction was quenched by the addition of 25% aqueous solution of NH4OAc. The reaction was extracted with EtOAc, dried over Na2SO4, evaporated in vacuo and purified by flash chromatography (20% EtOAc in hexane) to provide the title compound (770 mg).

Aufarbeitung

  1. customthe reaction was quenched by the addition of 25% aqueous solution of NH4OAc
  2. extractionThe reaction was extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. custompurified by flash chromatography (20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a915ee5f0f4549feb05435c9c9d1ea7b
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639780

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