反应 #811405

反应方程式

n-butyl lithium hexane

5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one

ammonium chloride

n-butyl lithium hexane

6-bromo-N-methyl-2-naphthamide

2-bromobenzotrifluoride

→

title compound

收率 44.6%

6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

收率 44.6%

溶剂

THF

THF

THF

反应条件

后处理

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

实验过程

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.

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