Acetaldehyde → 5-(2-Diethylamino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

Participants

Reaction Steps

To a suspension of 5-(2-amino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one methanesulfonic acid salt (from Example 11 above) (58.04 mg, 0.14 mmol) in CH2Cl2 (5 mL) were added acetaldehyde (Aldrich, 0.39 mg, 0.39 mmol) and sodium cyanoborohydride (Aldrich, 20.0 mg, 0.32 mmol) at room temperature. The reaction mixture was stirred for 1 hour. The reaction was then quenched with water (5 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were successively washed with water (5 mL) and brine (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with ethyl acetate and hexanes, filtered, and dried to give 5-(2-diethylamino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a brown solid. (Yield 12.0 mg, 23.4%).

Provenance & Evidence