Dimethyl Sulfate → 6-Bromo-3-methoxy-1,3-dimethylindolin-2-one

HRID 2209298

Reaktionsgleichung

Reaktionsgleichung von HRID 2209298
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](O)([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:14](=[O:17])([O-])[O-].[Cs+].[Cs+].S(OC)(O[CH3:24])(=O)=O>C(#N)C.CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([O:17][CH3:14])([CH3:12])[C:7](=[O:11])[N:8]2[CH3:24])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 665802586-Bromo-3-hydroxy-3-methylindolin-2-one

Produkt 1

HCID 894719146-Bromo-3-methoxy-1,3-dimethylindolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21891449acetonitrile N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 6-bromo-3-hydroxy-3-methylindolin-2-one 7.45 (200 mg, 0.826 mmol) in ACN/DMF (2:1, 6 mL) was cooled to 0° C. Cesium carbonate (942 mg, 2.89 mmol) and dimethyl sulfate (274 μL, 2.89 mmol) were added. The reaction was stirred at 0° C. for 90 min then at room temperature for 4 hours. The mixture was filtered over celite, concentrated and the residue was purified by flash column chromatography on silica gel to afford 6-bromo-3-methoxy-1,3-dimethylindolin-2-one 7.46. 1H NMR (400 MHz, DMSO-d6) δ 7.39-7.25 (m, 3H), 3.14 (s, 3H), 2.85 (s, 3H), 1.40 (s, 3H).

Aufarbeitung

  1. waitat room temperature for 4 hours
  2. filtrationThe mixture was filtered over celite,
  3. concentrationconcentrated
  4. customthe residue was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5a5b7068e3c449e6961fb87c97327213
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376441B2

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