2,2'-Bipyridine → (E)-tert-butyl 5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indole-1-carboxylate

HRID 587228노트

반응식

HRID 587228 반응식
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:7]=[CH:6]2)=[CH2:2].Br[CH:20]([C:25]1[CH:26]=[C:27]([Cl:33])[C:28]([F:32])=[C:29]([Cl:31])[CH:30]=1)[C:21]([F:24])([F:23])[F:22].N1C=CC=CC=1C1C=CC=CN=1>ClC1C=CC=CC=1Cl.Cl[Cu]>[Cl:31][C:29]1[CH:30]=[C:25]([CH:20]([C:21]([F:24])([F:23])[F:22])/[CH:2]=[CH:1]/[C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:7]=[CH:6]3)[CH:26]=[C:27]([Cl:33])[C:28]=1[F:32]

참가 물질

6

반응물 3

HCID 14742,2'-BipyridineHCID 66890900tert-Butyl 5-ethenyl-1H-indole-1-carboxylateHCID 866751625-(1-Bromo-2,2,2-trifluoroethyl)-1,3-dichloro-2-fluorobenzene

생성물 1

HCID 86675168(E)-tert-butyl 5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indole-1-carboxylate

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 72391,2-Dichlorobenzene용매

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온도
150 °C

실험 절차

To a stirred solution of tert-butyl 5-vinyl-1H-indole-1-carboxylate (0.65 g, 2.67 mmol), in 1,2-dichlorobenzene (10.0 mL) was added 5-(1-bromo-2,2,2-trifluoroethyl)-1,3-dichloro-2-fluorobenzene (1.74 g, 5.37 mmol), CuCl (53 mg, 0.537 mmol) and 2,2-bipyridyl (167 mg, 1.07 mmol). The resultant reaction mixture was degassed with argon for 30 min and heated to 150° C. for 2 h. The reaction mixture was cooled to ambient temperature and filtered, and the filtrate concentrated under reduced pressure. The crude compound was purified by column chromatography (SiO2, 100-200 mesh; 2% EtOAc/petroleum ether) to afford the title compound as a light brown gummy material (0.25 g, 10%): 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=8.0 Hz, 1H), 7.60 (m, 2H), 7.39 (m, 3H), 6.69 (d, J=16.0 Hz, 1H), 6.55 (d, J=10.5 Hz, 1H), 6.36 (dd, J=16.0, 8.0 Hz, 1H), 4.10 (m, 1H), 1.65 (s, 9H); ESIMS m/z 485.91 ([M−H]−); IR (thin film) 1165, 854 cm−1.

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 concentrated under reduced pressure
  6. customThe crude compound was purified by column chromatography (SiO2, 100-200 mesh; 2% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-3e1ca42d05e54a70a1b968a3d5e2c880
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226500B2

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