Cesium carbonate → 3-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide

HRID 925265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925265
[F:1][C:2]([F:13])([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH2:3][CH2:4][SH:5].F[C:15]1[C:16]([C:21]([NH:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:13][C:2]([F:1])([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH2:3][CH2:4][S:5][C:15]1[C:16]([C:21]([NH:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 867201623,3-Difluoro-3-(4-fluorophenyl)-propane-1-thiolHCID 867201633-fluoro-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide

Produkt 1

HCID 762874063-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amideAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 3,3-difluoro-3-(4-fluorophenyl)-propane-1-thiol (0.19 g, 0.92 mmol) in DMF (5 ml) in sealed tube are added 3-fluoro-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide (0.19 g, 0.92 mmol) and cesium carbonate (1.50 g, 4.60 mmol). The reaction mixture is heated at 90° C. for 2 h. After completion of the reaction, the reaction mixture is poured onto ice-water, extracted with EtOAc (3×30 ml). The combined organic layers are washed with brine (50 ml), water (30 ml), dried over sodium sulfate and evaporated to dryness to yield the crude product, which is purified by column chromatography (silica gel, 30% EtOAc/hexane) affording 3-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide (example 3) (0.15 g, 0.37 mmol, 41%). [M+H]+ 397.1.

Aufarbeitung

  1. customAfter completion of the reaction
  2. additionthe reaction mixture is poured onto ice-water
  3. extractionextracted with EtOAc (3×30 ml)
  4. washThe combined organic layers are washed with brine (50 ml), water (30 ml)
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customto yield the crude product, which
  8. customis purified by column chromatography (silica gel, 30% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b4e41457dbf64be0bb72c7a3d2f13bbb
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284286B2

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