1-Bromo-2-methylpropane → 4-carboxy-2-isobutyl-6-[4-(methylthio)phenyl)-2H-pyridazin-3-one

HRID 982787

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-methoxycarbonyl-6-[4-(methylthio)-phenyl]-2H-pyridazin-3-one (8.00 g, 29.0 mmol) in N,N-dimethylformamide (80 mL) were added potassium carbonate (8.02 g, 58.0 mmol) and isobutyl bromide (4.76 g, 34.8 mmol), and the mixture was stirred at 80° C. for 2 hours. The temperature of the reaction mixture was allowed to drop back to room temperature, and a saturated aqueous solution of sodium hydrogencarbonate was added. The mixture was then extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off. Following the procedure of the residue was reacted to yield the title compound as a yellow solid [yield: 65.1% (2 steps)].

Workup

customto drop back to room temperature
extractionThe mixture was then extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off
customwas reacted

Sources & evidence

ORD record: ord-68e83b782cca42b694f834baeaacea16
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06861428B2

Linked notes

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