Reaktion #983317

Reaktionsgleichung

1-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-2,5-dimethyl-1H-pyrrole

hydroxylamine hydrochloride

triethylamine

→

title compound

4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorobenzenamine

Lösungsmittel

ethanol THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is heated
2. 2
   Temperaturat reflux for 2 days
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   workup.ADDITIONdiluted with CH2Cl2 (60 mL)
5. 5
   Waschenwashed with water (3×20 mL)
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigePurification by chromatography on a Biotage Flash 40M 90 g silica gel cartridge
9. 9
   Wascheneluting with 10-20% EtOAC/Hexanes

Vorschrift

To a stirred solution of 1-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-2,5-dimethyl-1H-pyrrole (0.828 g, 2.71 mmol) in 95% ethanol/THF (10:1, 55 mL) is added hydroxylamine hydrochloride (3.77 g, 54.2 mmol) and triethylamine (3.8 mL, 27.1 mmol). The reaction mixture is heated at reflux for 2 days and then concentrated under reduced pressure, diluted with CH2Cl2 (60 mL), washed with water (3×20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Purification by chromatography on a Biotage Flash 40M 90 g silica gel cartridge, eluting with 10-20% EtOAC/Hexanes, affords the title compound, MS (ESI+) for C11H11F2NS m/z 228 (M+H)+; 1H NMR (CDCl3, 400 MHz) δ 6.22 (m, 2 H), 5.91 (m, 1 H), 3.83 (m, 2 H), 3.33 (m, 2 H), 2.86 (t, 2 H), 2.53 (m, 2 H).

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