Reaktionsgleichung
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+].C(Cl)Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:22]([C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[F:19])=[O:23])=[CH:14][CH:13]=2)=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of 4-(5-chloro-2-methylbenzoxazol-6-yl)phenylamine (56) (23 mg, 0.089 mmol) and 2 mg DMAP in 2 ml DCM was added 2-fluorobenzoyl chloride (21 μl, 0.18 mmol) followed by addition of DIEA (78 μl). The resulting brown solution was stirred at r.t. for 3 h. The reaction mixture was worked up with aq. NaHCO3/DCM. DCM phase was washed with brine, concentrated to dryness. The residue was dissolved in 2 ml THF/MeOH/H2O (5:4:1) and stirred with 1N NaOH (200 μl) at r.t. for 2 h before worked up with EA/aq. NaHCO3. Silica gel flash chromatography furnished 19.5 mg 57 as off-white solid. (yield: 57.5%).
Aufarbeitung
- washDCM phase was washed with brine
- concentrationconcentrated to dryness
- dissolutionThe residue was dissolved in 2 ml THF/MeOH/H2O (5:4:1)
- stirringstirred with 1N NaOH (200 μl) at r.t. for 2 h
Quellen und Nachweise
- ORD-Eintrag
- ord-d7bb26d50b9c4051b44a8a8e1adccd5b
- Quelldatensatz
- uspto-grants-2015_07
- Patentnummer
- US09090612B2
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