Sodium Carbonate → Methyl 3-methyl-2-(5-(4-nitrophenyl)-1,3-dioxoisoindolin-2-yl)butanoate

HRID 404123

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH:12]([CH:17]([CH3:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14])[C:5]2=[O:20].CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH3:18][CH:17]([CH3:19])[CH:12]([N:6]1[C:5](=[O:20])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)[CH:3]=2)[C:7]1=[O:11])[C:13]([O:15][CH3:16])=[O:14]

Participants

Conditions

Temperature: 80 °C

Procedure

The compound of example 660 (2.5 g, 7.35 mmol); 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (2.19 g, 8.82 mmol) and bis-Pinacolato diborane (180 mg, 0.22 mmol) were taken in dry DMF under argon atmosphere. Degassed 2M solution of sodium carbonate (1.94 g, 18.37 mmol) was added and the reaction mixture was heated to 80° C. for 2 h. The reaction mixture was cooled and the solvent was removed by distillation. The residue was taken in water and this aqueous mixture was extracted with ethyl acetate. The crude material was purified through column chromatography (silicagel, 30% dichloromethane in petroleum ether) to afford the title compound.

Workup

additionwas added
temperatureThe reaction mixture was cooled
customthe solvent was removed by distillation
extractionthis aqueous mixture was extracted with ethyl acetate
customThe crude material was purified through column chromatography (silicagel, 30% dichloromethane in petroleum ether)

Sources & evidence

ORD record: ord-e03ec7b9187b408fa0405e470797cf3e
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748426B2

Linked notes

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