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7-bromo-5-fluoro-1,2,3,4-tetrahydroisoquinolin-1-one[ No CAS ]
7-bromo-5-fluoro-1,2,3,4-tetrahydroquinolin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium azide; methanesulfonic acid; In dichloromethane; at 0 - 20℃; for 1.5h;
A solution of 6-bromo-4-fluoro-2,3-dihydro-lH-inden-l-one (500 mg, 2.18 mmol) in a mixture of DCM (13 mL) and methanesulfonic acid (6.5 mL) at 0C was treated slowly with sodium azide (115.32 mu, 3.27 mmol). The resulting mixture warmed to r.t. and stirred for 1.5 h. Ceric ammonium nitrate solution (5.5% in water, 25 mL) was added slowly and the mixture was partitioned between DCM (50 mL) and water (25 mL). The aqueous layer was extracted with DCM (50 mL), and the combined organic layers were washed with water (25 mL) and brine (25 mL), then dried (MgS04). The solvent was removed in vacuo to give a mixture (1 :1) of the title compounds (410 mg), that was used without separation
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 5h;
9.9.2 9.2 Preparation of 2-((benzyloxy)methyl)-7-bromo-5-fluoro-3,4-dihydroisoquinoline-1(2H)-one
7-Bromo-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one (2 g, 8.2 mmol) was dissolved in DMF (20 mL)Sodium hydrogen (656 mg, 16.4 mmol) was added, and after stirring for one hour, ((chloromethoxy)methyl)benzene (1.9 g, 12.2 mmol) was added, and the mixture was reacted at 20 ° C for 4 hours.After completion of the reaction, 100 mL of water and 50 mL of ethyl acetate were added, and the mixture was separated, and the aqueous phase was extracted with ethyl acetate (50 mL×2).The combined organic phase was concentrated and the residue was purified by column chromatography (petroleum ether: ethyl acetate = 10: 1) to give the product (2.3 g of, 76.7% yield).
7-bromo-5-fluoro-1,2,3,4-tetrahydroisoquinolin-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
45.3%
With sodium azide; methanesulfonic acid; In dichloromethane; at 0 - 20℃; for 2h;
6-Bromo-4-fluoro-2,3-dihydro-1H-inden-1-one (5 g, 21.8 mmol) was dissolved in dichloromethane (60 mL)Add a sodium azide (2.1 g, 32.3 mmol) at 0 C in a mixed solution of methanesulfonic acid (30 mL).The reaction was carried out at 20 C for 2 hours.After completion of the reaction, the reaction was quenched slowly with water at 0 C, then water (100 mL) and dichloromethane (50 mL).The liquid phase was separated, and the aqueous phase was extracted with dichloromethane (50 mL×2).The residue was purified by column chromatography (petroleum ether: ethyl acetate = 2: 1) to give the product (2.4g, yield 45.3%).
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