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

HRID 913674

Reaktionsgleichung

Reaktionsgleichung von HRID 913674
[C:1]([C:3]1[C:4]([C:20]([F:23])([F:22])[F:21])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13](=[NH:16])[NH:14][OH:15])[C:7]([CH2:17][CH2:18][CH3:19])=[CH:6]2)#[N:2].[Cl:24][C:25]1[C:30]([C:31](Cl)=O)=[CH:29][C:28]([Cl:34])=[CH:27][N:26]=1.C(N(CC)CC)C>C(#N)C>[Cl:24][C:25]1[C:30]([C:31]2[O:15][N:14]=[C:13]([CH2:12][N:8]3[C:9]4[C:5](=[C:4]([C:20]([F:22])([F:23])[F:21])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=4)[CH:6]=[C:7]3[CH2:17][CH2:18][CH3:19])[N:16]=2)=[CH:29][C:28]([Cl:34])=[CH:27][N:26]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27999962,5-Dichloro-nicotinoyl chlorideHCID 178438386HCID 178438386, Verbindung

Produkt 1

HCID 578003501-{[5-(2,5-Dichloro-3-pyridinyl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrileAusbeute 14,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 2-[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (Example 275A) (0.100 g, 0.308 mmol) in anhydrous acetonitrile (10.0 mL) under N2, was added 2,5-dichloro-3-pyridinecarbonyl chloride (0.223 g, 1.10 mmol) and triethylamine (1.0 mL, 13.6 mmol). The mixture was then heated in a microwave at 150° C. for 30 min. Upon cooling, the mixture was poured onto a biotage prepak column and the mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient) to give 0.021 g (14% yield) of pure product: MS (ES) m/z 480 (M+1).

Aufarbeitung

  1. temperatureUpon cooling
  2. additionthe mixture was poured onto a biotage prepak column
  3. customthe mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-cb1e382331b643dd81f573eeaaf3c750
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026262B2

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