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

HRID 404123

反応式

HRID 404123 の反応式
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]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 27735554,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolaneHCID 67305870Methyl 2-(5-bromo-1,3-dioxoisoindolin-2-yl)-3-methylbutanoate

生成物 1

HCID 67306305Methyl 3-methyl-2-(5-(4-nitrophenyl)-1,3-dioxoisoindolin-2-yl)butanoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e03ec7b9187b408fa0405e470797cf3e
出典データセット
uspto-grants-2014_06
特許番号
US08748426B2

関連ノート

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