Réaction #937938

Équation de réaction

10-bromo-2-hydroxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one

potassium carbonate

i-propyl bromoacetate

potassium iodide

→

title compound

Rendement 67.0%

10-bromo-5-methyl-2-i-propoxycarbonylmethyloxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

Rendement 67.0%

Solvants

dimethyl sulfoxide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 12 hours
2. 2
   Extractionextracted with ethyl acetate
3. 3
   LavageThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
4. 4
   Séchagedried over anhydrous sodium sulfate
5. 5
   Autrethe solvent was evaporated under reduced pressure
6. 6
   AutreThe residue was purified by silica gel flash column chromatography (eluent: ethyl acetate)
7. 7
   Autrethe crude purification product
8. 8
   Lavagewas washed with ether
9. 9
   Filtrationrecovered by filtration

Mode opératoire

10-bromo-2-hydroxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one (250 mg) obtained in Example 49 was suspended in dimethyl sulfoxide (10 ml), and potassium carbonate (210 mg) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and i-propyl bromoacetate (0.12 ml) and potassium iodide (1 grain) were added in succession, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice water (50 ml) and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: ethyl acetate), and the crude purification product was washed with ether and recovered by filtration to obtain the title compound (220 mg, 67%).

Source