Triethylamine → 1-({5-[2-Chloro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 913444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913444
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].CCN(CC)CC.[C:22]([C:24]1[C:25]([C:38]([F:41])([F:40])[F:39])=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][C:34](=[NH:37])[NH:35]O)[CH:28]=[CH:27]2)#[N:23]>CC#N>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]1[O:5][N:37]=[C:34]([CH2:33][N:29]2[C:30]3[C:26](=[C:25]([C:38]([F:41])([F:39])[F:40])[C:24]([C:22]#[N:23])=[CH:32][CH:31]=3)[CH:27]=[CH:28]2)[N:35]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27781062-Chloro-5-(trifluoromethyl)benzoyl chlorideHCID 178509476HCID 178509476, Verbindung

Produkt 1

HCID 249839911-({5-[2-Chloro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrileAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Chloro-5-(trifluoromethyl)benzoyl chloride (0.017 g, 0.071 mmol), Et3N (0.008 g. 0.078 mmol) and 2-[5-cyano-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (0.020 g, 0.071 mmol) were combined in CH3CN (1.5 mL). After stirring at rt for 1 h, the mixture was heated to 150° C. in a microwave for 10 min. Purification (SiO2, EtOAc/hexanes) afforded the title compound (0.025 g): MS (ESI): m/z 469 (M−1).

Aufarbeitung

  1. temperaturethe mixture was heated to 150° C. in a microwave for 10 min
  2. customPurification (SiO2, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-98ff143395b2492f8d1fdbacea8124e3
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026262B2

Notizen zur Reaktion

Wird geladen…