7-溴-3,4-二氢-1H-喹啉-2-酮

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a DMF solution (14.5 mL) of the compound (3.00 g) obtained in Step 1-2, zinc cyanide (1.04 g), Pd2(dba)3 (122 mg), Xantphos (154 mg) and TMEDA (590 μL) were added and the mixture was stirred under microwave irradiation (180° C.) for 5 minutes. To the reaction mixture, CHCl3 was added and the mixture was filtrated by Celite and washed with DMF. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60 N, mobile phase: EtOAc/hexane=50/50 to 100/0; v/v). To the solid substance obtained, EtOAc was added at room temperature and the mixture was stirred for 30 minutes. A solid substance was obtained by filtration and washed with EtOAc to obtain 2-oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile (15.5 g, a light yellow solid). the mixture was filtrated by Celite washed with DMF The filtrate was concentrated under reduced pressure The residue was purified by column chromatography (silica gel 60 N, mobile phase: EtOAc/hexane=50/50 to 100/0; v/v) To the solid substance obtained the mixture was stirred for 30 minutes A solid substance was obtained by filtration washed with EtOAc

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To the CHCl3 solution (560 mL) of the compound (39.5 g) obtained in Step 1-1 and methanesulfonic acid (122 mL), sodium azide (36.5 g) was added separately in parts under ice cooling, and then the mixture was heated to reflux for 2.5 hours. To H2O (400 mL), the reaction mixture was added under ice cooling, adjusted to pH 9 with 28% ammonia water and extracted with CHCl3 three times. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. Thereafter, the residue was purified by column chromatography (silica gel 60 N, mobile phase: EtOAc/hexane=50/50 to 75/25; v/v). The solid substance obtained was suspended in a solution of EtOAc/hexane (1/1; v/v) and the mixture was stirred at room temperature for one hour. A solid substance was obtained by filtration to give 7-bromo-3,4-dihydroquinolin-2(1H)-one (15.5 g, a light yellow solid). the mixture was heated to reflux for 2.5 hours extracted with CHCl3 three times The combined organic layers were dried over Na2SO4 concentrated under reduced pressure Thereafter, the residue was purified by column chromatography (silica gel 60 N, mobile phase: EtOAc/hexane=50/50 to 75/25; v/v) The solid substance obtained A solid substance was obtained by filtration