反応 #90133

反応方程式

4-bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

sodium azide

(1S,2S)—N,N′-dimethyl-cyclohexane-1,2-diamine

sodium ascorbate

sodium hydroxide

→

title compound

収率 27.0%

4-Amino-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

収率 27.0%

溶媒

water

ethanol

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   洗浄washed with water and saturated brine
3. 3
   乾燥dried over sodium sulfate
4. 4
   ろ過filtered
5. 5
   その他The residues obtained
6. 6
   濃縮after concentration under reduced pressure
7. 7
   その他were purified by silica gel column chromatography (methanol/dichloromethane)

実験手順

Under nitrogen atmosphere, 4-bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound U5, 25.0 mg, 63.25 μmol), copper iodide (2.41 mg, 12.65 μmol), sodium azide (20.6 mg, 316.3 μmol), (1S,2S)—N,N′-dimethyl-cyclohexane-1,2-diamine (2.70 mg, 18.98 μmol), and sodium ascorbate (1.25 mg, 6.325 μmol) were dissolved in ethanol (0.70 mL) and water (0.30 mL) and the mixture was stirred at 100° C. for 2 hr. The reaction solution was poured into aqueous solution of sodium hydroxide (1 M), extracted with ethyl acetate, washed with water and saturated brine, dried over sodium sulfate, and then filtered. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (methanol/dichloromethane) to obtain the title compound (5.6 mg, 27%).

出典