反应详情

温度

-65 °C

Under an argon atmosphere, 2-bromobenzotrifluoride (33.05 g) was dissolved in dry THF (600 ml), and the mixture was cooled to −65° C. in a dry ice-acetone bath. An n-butyl lithium hexane solution (1.6M: 93.7 ml) was added with stirring and the mixture was stirred at the same temperature for 30 min. After stirring the mixture, a dry THF (2.88L) solution of 6-bromo-N-methyl-2-naphthamide (38.03 g) cooled to 10° C. was added at not more than −55° C. The mixture was stirred for 20 min. An n-butyl lithium hexane solution (1.6M: 94.5 ml) was added at not more than −65° C. The mixture was stirred for 30 min and 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (14.66 g) in a dry THF solution (240 ml) was added dropwise. The mixture was stirred at the same temperature for 1.5 h and saturated aqueous ammonium chloride solution (520 ml) was added to stop the reaction. The solvent was evaporated under reduced pressure and an ethanol-soluble material was extracted from the resulting residue and the solvent was evaporated again. The resulting residue was purified by flash silica gel column chromatography (eluent; chloroform/methanol containing ammonia (7%); 19/1→9/1). The eluate was recrystallized from methanol to give the title compound (16.44 g) as colorless crystals. The physical and chemical data were identical with those of the compound obtained in Example 5.

1. stirringthe mixture was stirred at the same temperature for 30 min
2. stirringAfter stirring the mixture
3. additionwas added at not more than −55° C
4. stirringThe mixture was stirred for 20 min
5. stirringThe mixture was stirred for 30 min
6. stirringThe mixture was stirred at the same temperature for 1.5 h
7. customthe reaction
8. customThe solvent was evaporated under reduced pressure
9. extractionan ethanol-soluble material was extracted from the resulting residue
10. customthe solvent was evaporated again
11. customThe resulting residue was purified by flash silica gel column chromatography (eluent; chloroform/methanol containing ammonia (7%); 19/1→9/1)
12. customThe eluate was recrystallized from methanol