1-Bromo-2-methylpropane → 6-(3-fluoro-4-methylphenyl)-2-isobutyl-4-methoxycarbonyl-2H-pyridazin-3-one

HRID 7911

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[C:12](=[O:15])[NH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH:27]([CH3:29])[CH3:28].C(=O)([O-])O.[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[C:12](=[O:15])[N:13]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 80 °C

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%).

Workup

customto drop back to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customThe residue was purified by column chromatography on silica gel [silica gel 100 g, chloroform/methanol (100/1→50/1))

Sources & evidence

ORD record: ord-447057a76e4c472e8ee185e270a27f68
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087606B2

Linked notes

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