Cesium carbonate → 6-Bromo-1-(3-fluorobenzyl)indoline

HRID 871073

Reaktionsgleichung

Reaktionsgleichung von HRID 871073
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][CH:3]=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 680073-Fluorobenzyl bromideHCID 130983796-Bromo-2,3-dihydro-1H-indole

Produkt 1

HCID 904086526-Bromo-1-(3-fluorobenzyl)indoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 6-bromoindoline (750 mg, 3.79 mmol), 1-(bromomethyl)-3-fluorobenzene (697 pt, 5.68 mmol) and cesium carbonate (1.851 g, 5.68 mmol) in N,N-dimethylformamide (7.573 mL) was stirred at 110° C. for 2 hours. The mixture was cooled, diluted with 100 mL ethyl acetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel flash chromatography (Isco®, Redi-Sep® column), eluting with a gradient of 2-50% ethyl acetate/hexane, afforded the title compound. LCMS: 306 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel flash chromatography (Isco®, Redi-Sep® column)
  7. washeluting with a gradient of 2-50% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-88a32b9c0dec4ded89645f7fd044b689
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969375B2

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