Reaktionsgleichung
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)([N:3]1C=CN=C1)=[O:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2C=CN=C(NN)[C:21]=2[C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:16][CH:15]=1.O>C1COCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:11]=[CH:12][N:8]3[C:1](=[O:2])[NH:3][N:10]=[C:9]3[C:21]=2[C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)=[CH:18][CH:19]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirring solution of 1,1′-carbonyldiimidazole (2.5 g, 15.4 mmol) in THF (15 mL) at room temperature under argon was added 4-(4-chlorophenyl)-2-hydrazinyl-3,4′-bipyridine (0.92 g, 3.1 mmol). The reaction mixture was stirred at room temperature for 45 min. The reaction mixture was then concentrated under vacuum to produce a yellow solid. This solid was stirred in an ice bath and water (25 mL) was added. Solid was collected by filtration and further washed with water (15 mL×2). After drying in an oven at 50° C. under reduced pressure overnight, 960 mg of the title compound was obtained as a yellow solid. HPLC/MS: retention time=1.985 min, [M+H]+=323. 1H NMR (DMSO-d6, 500 MHz): δ 12.61 (s, 1H), 8.50 (d, J=6.05 Hz, 2H), 7.94 (d, J=7.15 Hz, 1H), 7.36 (d, J=8.2 Hz, 2H), 7.23 (d, J=6.05 Hz, 2H), 7.18 (d, J=8.2 Hz, 2H), 6.68 (d, J=7.15 Hz, 1H).
Aufarbeitung
- concentrationThe reaction mixture was then concentrated under vacuum
- customto produce a yellow solid
- stirringThis solid was stirred in an ice bath
- filtrationSolid was collected by filtration
- washfurther washed with water (15 mL×2)
- customAfter drying in an oven at 50° C. under reduced pressure overnight
Quellen und Nachweise
- ORD-Eintrag
- ord-e63319b9eae244999cc3c33bb32e754e
- Quelldatensatz
- uspto-grants-2009_08
- Patentnummer
- US07572808B2
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