A kind of synthetic method of quinoxaline pharmaceutical intermediate compound
A synthesis method and compound technology, which are applied in the synthesis of nitrogen-containing fused ring compounds and the synthesis of quinoxaline pharmaceutical intermediate compounds, can solve the problems of poor atom economy, insufficient substrate sources, and unsatisfactory yields. Achieve the effects of high yield, good industrial application prospect and potential
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Embodiment 1
[0044] Example 1: Synthesis of 6-chloro-2,3-diphenylquinoxaline
[0045]
[0046] In 400ml DMSO, add 100mmol of formula (II) compound, 100mmol of formula (III) compound (1,2-dibromo-1,2-diphenylethane), 1mmol dichlorodiammine platinum, 1.5mmol 4, 7-Dimethyl-1,10-phenanthroline, 200mmol of diisopropanolamine and 10mmol of N-hexylpyridine hexafluorophosphate, and then nitrogen purge twice to make the reaction atmosphere a nitrogen atmosphere; the reaction system from room temperature The temperature was raised to 80°C, and the reaction was stirred at this temperature for 12 hours.
[0047] After the reaction, the reaction system was naturally cooled to room temperature, and then washed with saturated brine. The camera was separated and the organic phase was concentrated in vacuo. The residue was subjected to 200 mesh silica gel column chromatography using petroleum ether and chloroform in a volume ratio of 2:1 As the eluent, the target compound of formula (I) 6-chloro-2,3-diphenylqu...
Embodiment 2
[0051] Example 2: Synthesis of 6-Methoxyquinoxaline
[0052]
[0053] In 400ml NMP, add 100mmol of formula (II) compound, 150mmol of formula (III) compound (1,2-dibromoethane), 3mmol dichlorodiammine platinum, 6mmol 4,7-dimethyl-1,10 -Phenanthroline, 250mmol diisopropanolamine and 20mmol N-hexylpyridine hexafluorophosphate, and then nitrogen purge twice to make the reaction atmosphere a nitrogen atmosphere; the reaction system is raised from room temperature to 100°C, and The reaction was stirred at temperature for 10 hours.
[0054] After the reaction, the reaction system was naturally cooled to room temperature, and then washed with saturated brine. The camera was separated and the organic phase was concentrated in vacuo. The residue was subjected to 200-mesh silica gel column chromatography using petroleum ether and chloroform in a volume ratio of 3:1 As the eluent, the target compound of formula (I) 6-methoxyquinoxaline was obtained with a yield of 98.4%.
[0055] 1 H-NMR (400M...
Embodiment 3
[0057] Example 3: Synthesis of 6,7-dimethyl-2-phenylquinoxaline
[0058]
[0059] In 400ml of toluene, add 100mmol of formula (II) compound, 200mmol of formula (III) compound (1,2-dibromoethylbenzene), 5mmol dichlorodiammine platinum, 12mmol 4,7-dimethyl-1, 10-phenanthroline, 300mmol diisopropanolamine and 30mmol N-hexylpyridine hexafluorophosphate, and then nitrogen purge twice to make the reaction atmosphere a nitrogen atmosphere; the reaction system was raised from room temperature to 120 ℃, and The reaction was stirred at this temperature for 8 hours.
[0060] After the reaction, the reaction system was naturally cooled to room temperature, and then washed with saturated brine. The camera was separated and the organic phase was concentrated in vacuo. The residue was subjected to 200 mesh silica gel column chromatography using petroleum ether and chloroform in a volume ratio of 4:1 As the eluent, the target compound of formula (I) 6,7-dimethyl-2-phenylquinoxaline was obtained w...
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