Reaktion #2148161

Reaktionsgleichung

1,2-dibromoethane

Cs2CO3

5,7-diBOC-2,10-difluoro-6-hydroxyindolo[2,3-b]carbazole

→

5,7-diBOC-2,10-difluoro-6-(2-bromoethoxy)indolo[2,3-b]carbazole

Ausbeute 77.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe suspension was refluxed
2. 2
   SonstigeAfter completion of the reaction (1-3 hours)
3. 3
   Sonstigethe solid was removed by filtration
4. 4
   Waschenwashed with dichloromethane
5. 5
   EinengenThe combined filtrate was concentrated
6. 6
   Wascheneluting with 8% ethyl acetate in hexanes

Vorschrift

To a solution of 1,2-dibromoethane (>5 equiv) in acetonitrile was added Cs2CO3 (2 equiv) and 5,7-diBOC-2,10-difluoro-6-hydroxyindolo[2,3-b]carbazole (1 equiv) under argon. The suspension was refluxed and the reaction was monitored by TLC. After completion of the reaction (1-3 hours), the solid was removed by filtration and washed with dichloromethane. The combined filtrate was concentrated and the residue was subjected to chromatography on silica gel, eluting with 8% ethyl acetate in hexanes to give 5,7-diBOC-2,10-difluoro-6-(2-bromoethoxy)indolo[2,3-b]carbazole (77%). 1H NMR (400 MHz, CDCl3) δ ppm 8.13 (s, 1H), 8.06 (dd, J=9.0, 4.2 Hz, 2H), 7.68 (dd, J=8.4, 2.8 Hz, 2H), 7.17 (td, J=9.0, 2.8 Hz, 2H), 4.21 (t, J=6.8 Hz, 2H), 3.42 (t, J=7.0 Hz, 2H), 1.74 (s, 18H).

Quelle