Reaktionsgleichung
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[C:24]2[C:19](=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][N:16]=1>C1COCC1>[N+:25]([C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:19]=1[N:18]=[CH:17][N:16]=[C:15]2[O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)([O-:27])=[O:26]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 3-(trifluoromethyl)phenol (726 mg, 4.48 mmol) in THF (2 mL) was added NaH (179 mg, 4.48 mmol, 60% in mineral oil) at 0° C. and the reaction mixture was stirred for 15 min. Then a solution of 4-chloro-8-nitroquinazoline (Intermediate-7, step 2, 470 mg, 2.24 mmol) in THF (3 mL) was added to the reaction mixture at the same temperature and the reaction mixture was stirred at rt for 4 h. Then the reaction mixture was quenched with 1N HCl at 0° C. and the precipitate obtained was filtered and purified by column chromatography using 5-10% EtOAc in petroleum ether to afford 430 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.88 (s, 1H), 8.68 (d, J=7.8 Hz, 1H), 8.60 (d, J=7.2 Hz, 1H), 7.99-7.94 (t, J=8.4 Hz, 1H), 7.89 (s, 1H), 7.77 (s, 3H); MS (m/z): 336.12 (M+H)+.
Aufarbeitung
- stirringthe reaction mixture was stirred at rt for 4 h
- customThen the reaction mixture was quenched with 1N HCl at 0° C.
- customthe precipitate obtained
- filtrationwas filtered
- custompurified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-4bc87d0977fb4c2986f96fc5b1275c56
- Quelldatensatz
- uspto-grants-2015_04
- Patentnummer
- US09006257B2
Verknüpfte Notizen
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