Reaction #8007

Reaction equation

sodium hydrogencarbonate

6-(3-fluoro-4-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one

potassium carbonate

isobutyl bromide

→

title compound

Yield 85.0%

6-(3-fluoro-4-methylphenyl)-2-isobutyl-4-methoxycarbonyl-2H-pyridazin-3-one

Yield 85.0%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Otherto drop back to room temperature
2. 2
   Extractionthe mixture was extracted with ethyl acetate
3. 3
   WashThe extract was washed with brine
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   OtherThe residue was purified by column chromatography on silica gel [silica gel 100 g, chloroform/methanol (100/1→50/1))

Procedure

To a solution of 6-(3-fluoro-4-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one (5.28 g, 20.0 mmol) in N,N-dimethylformamide (40 mL) were added potassium carbonate (5.53 g, 40.0 mmol) and isobutyl bromide (3.29 g, 24.0 mmol), and the mixture was stirred at 80° C. for 1 hour. The temperature of the reaction mixture was allowed to drop back to room temperature. A saturated aqueous solution of sodium hydrogencarbonate was added, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel [silica gel 100 g, chloroform/methanol (100/1→50/1)) to yield the title compound as an orange oil (5.41 g, 84.9%).

Source