Reaktion #2148145

Reaktionsgleichung

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

tert-butyl 3-bromopropylcarbamate

Cs2CO3

→

3-(2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)propan-1-amine

Ausbeute 82.0%

Lösungsmittel

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(˜2 h)
2. 2
   TemperaturAfter cooled to RT
3. 3
   Sonstigethe inorganic salt was removed by filtration
4. 4
   Waschenwashed with dichloromethane
5. 5
   Einengenthe combined filtrate was concentrated
6. 6
   workup.DISSOLUTIONThe resulting residue 3-(2,10-difluoro-5,7-diBOC-indolo[2,3-b]carbazol-6-yloxy)propan-1-amine was dissolved in CH2Cl2 (100 mL)
7. 7
   workup.ADDITIONTFA (10 mL) was added
8. 8
   SonstigeAfter evaporation
9. 9
   Wascheneluting with ethyl acetate/hexane/MeOH (10% cNH3.H2O) (50/50/10-100/0/10)

Vorschrift

A mixture of 5,7-diBOC-2,10-difluoro-6-hydroxyindolo[2,3-b]carbazole (4.03 g, 8.0 mmol), tert-butyl 3-bromopropylcarbamate (2.20 g, 9.2 mmol), and Cs2CO3 (10.0 g, 31 mmol), and anhydrous MeCN (120 mL) was heated at 100° C. under Ar until the starting material disappeared (˜2 h). After cooled to RT, the inorganic salt was removed by filtration, washed with dichloromethane, and the combined filtrate was concentrated. The resulting residue 3-(2,10-difluoro-5,7-diBOC-indolo[2,3-b]carbazol-6-yloxy)propan-1-amine was dissolved in CH2Cl2 (100 mL). TFA (10 mL) was added and the solution was stirred at RT overnight. After evaporation, the residue was subjected to chromatography on silica gel, eluting with ethyl acetate/hexane/MeOH (10% cNH3.H2O) (50/50/10-100/0/10), giving 2.35 g (82%) of 3-(2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)propan-1-amine. 1H NMR (400 MHz, DMSO-d6) δ 11.8 (br s, 2H), 8.56 (s, 1H), 7.89 (dd, J=9.4, 2.6 Hz, 2H), 7.44 (dd, J=8.6, 4.6 Hz, 2H), 7.17 (td, J=9.2, 2.4 Hz, 2H), 4.36 (t, J=6.2 Hz, 2H), 2.97 (t, J=6.2 Hz, 2H), 1.98 (pentalet, J=6.2 Hz, 2H).

Quelle