2,2'-Bipyridine → (E)-2-(2-chloro-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)benzyl)isoindoline-1,3-dione

HRID 1502859노트

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HRID 1502859 반응식
[Cl:1][C:2]1[CH:19]=[C:18]([CH:20]=[CH2:21])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].Br[CH:23]([C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=1)[C:24]([F:27])([F:26])[F:25].N1C=CC=CC=1C1C=CC=CN=1>ClC1C=CC=CC=1Cl.Cl[Cu]>[Cl:1][C:2]1[CH:19]=[C:18](/[CH:20]=[CH:21]/[CH:23]([C:28]2[CH:29]=[C:30]([Cl:35])[CH:31]=[C:32]([Cl:34])[CH:33]=2)[C:24]([F:27])([F:26])[F:25])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]

참가 물질

6

반응물 3

HCID 14742,2'-BipyridineHCID 866751181-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzeneHCID 866751792-(2-Chloro-4-vinylbenzyl)isoindoline-1,3-dione

생성물 1

HCID 86675180(E)-2-(2-chloro-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)benzyl)isoindoline-1,3-dione수율 50%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 72391,2-Dichlorobenzene용매

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온도
180 °C

실험 절차

To a stirred solution of 2-(2-chloro-4-vinylbenzyl)isoindoline-1,3-dione (2.0 g, 6.51 mmol) in 1,2-dichlorobenzene (25 mL) were added 1-(1-bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (3.48 g, 11.36 mmol), CuCl (112 mg, 1.13 mmol) and 2,2-bipyridyl (0.35 g). The resultant reaction mixture was degassed with argon for 30 min and then was stirred at 180° C. for 24 h. After the reaction was deemed complete by TLC, the reaction mixture was cooled to ambient temperature and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in n-hexane) to afford the title compound as solid (1.3 g, 50%): mp 141-143° C.; 1H NMR (400 MHz, CDCl3) δ 7.92 (m, 2H), 7.79 (m, 2H), 7.42 (m, 2H), 7.24 (m, 2H), 7.20 (m, 2H), 6.54 (d, J=16.0 Hz, 1H), 6.34 (dd, J=16.0, 8.0 Hz, 1H), 5.00 (s, 2H), 4.10 (m, 1H); ESIMS m/z 524.07 ([M+H]+).

후처리

  1. customThe resultant reaction mixture
  2. customwas degassed with argon for 30 min
  3. temperaturethe reaction mixture was cooled to ambient temperature
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in n-hexane)

출처 및 근거

ORD 기록
ord-016ea254503942d5b6572a152f65eae4
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09211280B2

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