2,2'-Bipyridine → (E)-1-(4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)phenyl)-1H-1,2,4-triazole

HRID 1502765노트

반응식

HRID 1502765 반응식
Br[CH:2]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([Cl:14])[CH:8]=1)[C:3]([F:6])([F:5])[F:4].[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)=[CH:19][CH:18]=1)=[CH2:16].N1C=CC=CC=1C1C=CC=CN=1>ClC1C=CC=CC=1Cl.Cl[Cu]>[Cl:14][C:9]1[CH:8]=[C:7]([CH:2]([C:3]([F:6])([F:5])[F:4])/[CH:16]=[CH:15]/[C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH:27]=[N:26][CH:25]=[N:24]3)=[CH:21][CH:22]=2)[CH:12]=[C:11]([Cl:13])[CH:10]=1

참가 물질

6

반응물 3

HCID 14742,2'-BipyridineHCID 585499641-(4-vinylphenyl)-1H-1,2,4-triazoleHCID 866751181-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene

생성물 1

HCID 86675223(E)-1-(4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)phenyl)-1H-1,2,4-triazole수율 32%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 72391,2-Dichlorobenzene용매

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온도
180 °C

실험 절차

To a stirred solution of 1-(1-bromo-2,2,2-trifluoro-ethyl)-3,5-dichloro-benzene (2.0 g, 6.51 mmol) in 1,2-dichlorobenzene (25 mL), were added 1-(4-vinyl-phenyl)-1H-[1,2,4]triazole (2.22 g, 13.0 mmol), CuCl (64 mg, 0.65 mmol) and 2,2-bipyridyl (0.2 g, 1.3 mmol). The resultant reaction mixture was degassed with argon for 30 min, then stirred at 180° C. for 24 h. After completion of reaction (TLC), the reaction mixture was cooled to ambient temperature and filtered and the filtrate concentrated under reduced pressure. Purification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether) afforded the title compound as an off-white solid (0.8 g, 32%): mp 93-97° C.; 1H NMR (300 MHz, CDCl3) δ 8.56 (s, 1H), 8.11 (s, 1H), 7.68 (d, J=8.4 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.38 (t, J=1.8 Hz, 1H), 7.29 (s, 2H), 6.62 (d, J=15.6 Hz, 1H), 6.42 (dd, J=15.6, 8.2 Hz, 1H), 4.15 (m, 1H); ESIMS m/z 398.05 ([M+H]+).

후처리

  1. customThe resultant reaction mixture
  2. customwas degassed with argon for 30 min
  3. customAfter completion of reaction (TLC)
  4. temperaturethe reaction mixture was cooled to ambient temperature
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customPurification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-cb6d6bdf239f404da3e4f86dbe7e7d97
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09210927B2

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