2,2'-Bipyridine → (E)-2-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)phenylamino) isoindoline-1,3-dione

HRID 587258ノート

反応式

HRID 587258 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:5][CH:4]=1)=[CH2:2].N1C=CC=CC=1C1C=CC=CN=1.Br[CH:34]([C:39]1[CH:40]=[C:41]([Cl:47])[C:42]([Cl:46])=[C:43]([Cl:45])[CH:44]=1)[C:35]([F:38])([F:37])[F:36]>ClC1C=CC=CC=1Cl.Cl[Cu]>[F:38][C:35]([F:36])([F:37])[CH:34]([C:39]1[CH:40]=[C:41]([Cl:47])[C:42]([Cl:46])=[C:43]([Cl:45])[CH:44]=1)/[CH:2]=[CH:1]/[C:3]1[CH:4]=[CH:5][C:6]([NH:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 14742,2'-BipyridineHCID 866751531-(1-Bromo-2,2,2-trifluoroethyl)-3,4,5-trichlorobenzeneHCID 866751912-(4-Vinylphenylamino)isoindoline-1,3-dione

生成物 1

HCID 86675192(E)-2-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)phenylamino) isoindoline-1,3-dione収率 77.8%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 72391,2-Dichlorobenzene溶媒

反応条件

温度
180 °C

実験手順

To a stirred solution of 2-(4-vinylphenylamino)isoindoline-1,3-dione (0.3 g, 1.1 mmol) in 1,2-dichlorobenzene (5 mL) were added CuCl (0.022 g, 0.273 mmol), 2,2-bipyridyl (0.07 g, 0.46 mmol) and 5-(1-bromo-2,2,2-trifluoroethyl)-1,2,3-trichlorobenzene (0.77 g, 2.27 mmol). The reaction mixture was degassed with argon for 30 min and was heated at 180° C. for 2 h. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by column chromatography (SiO2, 0-30% EtOAc in petroleum ether) to afford the title compound as a solid (450 mg, 75%): mp 187-189° C.; 1H NMR (400 MHz, CDCl3) δ 8.75 (s, 1H), 7.96 (m, 4H), 7.82 (s, 2H), 7.37 (d, J=8.8 Hz, 1H), 6.73 (d, J=8.4 Hz, 2H), 6.61 (m, 2H), 6.58 (m, 1H), 4.59 (m, 1H); ESIMS m/z 523.05 ([M−H]−).

後処理

  1. customThe reaction mixture was degassed with argon for 30 min
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customthe residue was purified by column chromatography (SiO2, 0-30% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-89bdfe7f02a841499dfa780a39680eff
出典データセット
uspto-grants-2016_01
特許番号
US09226500B2

反応ノート

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