Triethylamine → 4-{5-[(E)-2-{4-(2-Chlorophenyl)-5-[5-(methylsulfonyl)-2-pyridinyl]-4H-1,2,4-triazol-3-yl}vinyl]-1,3,4-oxadiazol-2-yl}benzonitrile

HRID 1478118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478118
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)=[N:11][N:10]=[C:9]1/[CH:23]=[CH:24]/[C:25]([NH:27][NH:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)=[N:11][N:10]=[C:9]1/[CH:23]=[CH:24]/[C:25]1[O:38][C:29]([C:30]2[CH:31]=[CH:32][C:33]([C:36]#[N:37])=[CH:34][CH:35]=2)=[N:28][N:27]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67958722HCID 67958722, Verbindung

Produkt 1

HCID 679601344-{5-[(E)-2-{4-(2-Chlorophenyl)-5-[5-(methylsulfonyl)-2-pyridinyl]-4H-1,2,4-triazol-3-yl}vinyl]-1,3,4-oxadiazol-2-yl}benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(E)-N′-(3-(4-(2-chlorophenyl)-5-(5-(methylsulfonyl)pyridin-2-yl)-4H-1,2,4-triazol-3-yl)acryloyl)-4-cyanobenzohydrazide 10 was dissolved into dichloromethane (10 mL) and triphenyl phosphine (0.27 g, 1.0 mmol), carbon tetrabromide (0.34 g, 1.04 mmol) and triethylamine (0.18 mL, 1.30 mmol) was added. The reaction was kept at ambient temperature for 2 h. The final compound was purified by column chromatography (eluting with hexane and ethyl acetate 1:3) to give (E)-4-(5-(2-(4-(2-chlorophenyl)-5-(5-(methylsulfonyl)pyridin-2-yl)-4H-1,2,4-triazol-3-yl)vinyl)-1,3,4-oxadiazol-2-yl)benzonitrile as a yellow solid. Yield: 0.035 g, 12.7%.

Aufarbeitung

  1. additionwas added
  2. customThe final compound was purified by column chromatography (eluting with hexane and ethyl acetate 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-44993116bf1c4cc1a1612e8e7739b26b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403812B2

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