반응 #90133

반응 방정식

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

수율 27.0%

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

수율 27.0%

용매

water

ethanol

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate
2. 2
   세척washed with water and saturated brine
3. 3
   건조dried over sodium sulfate
4. 4
   여과filtered
5. 5
   기타The residues obtained
6. 6
   농축after concentration under reduced pressure
7. 7
   기타were purified by silica gel column chromatography (methanol/dichloromethane)

실험 절차

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%).

출처