تفاعل #90133

معادلة التفاعل

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

المردود 27.0%

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

المردود 27.0%

المذيبات

water

ethanol

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with ethyl acetate
2. 2
   غسيلwashed with water and saturated brine
3. 3
   تجفيفdried over sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   أخرىThe residues obtained
6. 6
   تركيزafter concentration under reduced pressure
7. 7
   أخرىwere purified by silica gel column chromatography (methanol/dichloromethane)

الإجراء التجريبي

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%).

المصدر