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

HRID 587729ノート

反応式

HRID 587729 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, O-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

出典と根拠

ORDレコード
ord-c843d3797fc84cd3856742acaddb419f
出典データセット
uspto-grants-2016_01
特許番号
US09226501B2

反応ノート

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