Reaktion #2510318

Reaktionsgleichung

Triethylamine

tert-Butyl 8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate

Intermediate 17

tert-Butyl 8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate

1-fluoro-2-iodoethane

TFA

→

title compound

2-(2-Fluoroethyl)-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturto reflux
3. 3
   SonstigeThe solution was evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in DMF (0.5 mL)
5. 5
   workup.ADDITIONwas added
6. 6
   SonstigeThe solution was evaporated
7. 7
   Sonstigethe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Vorschrift

tert-Butyl 8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 17, 16 mg, 0.040 mmol) was dissolved in DCM (1 mL) and TFA (0.5 mL) was added. The reaction mixture was heated to reflux, and immediately allowed to cool to room temperature. The solution was evaporated and the residue was dissolved in DMF (0.5 mL). Triethylamine (0.011 mL, 0.080 mmol) was added and the reaction mixture was stirred for 5 minutes before 1-fluoro-2-iodoethane (0.063 mL, 0.080 mmol) was added. The solution was stirred at 60° C. overnight. The solution was evaporated and the crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (6.9 mg). MS m/z 375 [M+H]+.

Quelle