Reaktion #1568596

Reaktionsgleichung

water

2-(4-Chlorophenyl)-2-methyloxirane

sodium hydride

9-chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

→

1-(9-chloro-3-methyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-2-(4-chlorophenyl)propan-2-ol

Ausbeute 43.6%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe title compound was prepared
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGstirred at RT for 14 h
4. 4
   workup.ADDITIONwas added
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
7. 7
   Sonstigeevaporated under reduced pressure
8. 8
   Sonstigepurified by reverse phase chromatography

Vorschrift

The title compound was prepared by following general procedure 5. To a stirred suspension of sodium hydride (61 mg, 0.254 mmol) in 5 mL of DMF, 9-chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.2 g, 0.852 mmol) was added and stirred at RT for 5 min. 2-(4-Chlorophenyl)-2-methyloxirane (214 mg, 1.27 mmol) was added slowly dropwise and stirred at RT for 14 h. The reaction was monitored by TLC and LCMS. After completion of the reaction, water was added, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, evaporated under reduced pressure and purified by reverse phase chromatography to afford 150 mg of (1-(9-chloro-3-methyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-2-(4-chlorophenyl)propan-2-ol) as the TFA salt.

Quelle