Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][N:7]=[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH:5]=1>CCO>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([NH2:10])=[CH:8][N:7]=[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH:5]=1Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Compound (1B) (7.99 g, 25.6 mmol) was taken up in EtOH (350 mL), and nitrogen gas was bubbled through the solution for five minutes before 10% Pd/C (1.6 g) was carefully added. The resulting mixture was put on the Parr Shaker under 60 psi hydrogen gas for 4 hours. By TLC, there was no starting material remaining. The reaction mixture was filtered through a 3 cm bed of celite, and the filtrate was concentrated to give 7.0 g of crude product. Purification by column chromatography eluting on 130 g of silica gel with a gradient of 5% EtOAc in hexanes through 10% EtOAc in hexanes afforded the titled compound (1C) as an off-white powder (4.223 g, (M+H)+=281, Mp=102.0–103.9° C.).
Aufarbeitung
- customnitrogen gas was bubbled through the solution for five minutes before 10% Pd/C (1.6 g)
- additionwas carefully added
- filtrationThe reaction mixture was filtered through a 3 cm bed of celite
- concentrationthe filtrate was concentrated
- customto give 7.0 g of crude product
- customPurification by column chromatography
- washeluting on 130 g of silica gel with a gradient of 5% EtOAc in hexanes through 10% EtOAc in hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-e9826071e24d4442987697b7a98e068c
- Quelldatensatz
- uspto-grants-2007_03
- Patentnummer
- US07189731B2
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