Potassium Carbonate → 4-(2,3-Dimethyl-4-nitrophenoxy)pyridin-2-amine
Reaktionsgleichung
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([CH3:19])[C:11]=1[CH3:20].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:20][C:11]1[C:12]([CH3:19])=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 75 °C
Versuchsvorschrift
To a stirred solution of 2-aminopyridin-4-ol (600 mg, 5.5 mmol) and 1-fluoro-2,3-dimethyl-4-nitrobenzene (570 mg, 3.37 mmol) in DMSO (4.0 mL) was added K2CO3 (1.00 g, 7.20 mmol) and the reaction mixture heated to 75° C. for 3 days. The resulting mixture was cooled to RT and was partitioned between water (50 mL) and EtOAc (75 mL). The aq layer was separated and extracted with EtOAc (75 mL) and the combined organic extracts were washed with water (3×50 mL) and brine (50 mL) and then dried and evaporated in vacuo. The residue was recrystallized from DCM to afford the title compound, Intermediate C2, as a tan solid (25 mg, 28%): Rt 1.40 min (Method 2); m/z 260 (M+H)+ (ES+).
Aufarbeitung
- temperatureThe resulting mixture was cooled to RT
- customwas partitioned between water (50 mL) and EtOAc (75 mL)
- customThe aq layer was separated
- extractionextracted with EtOAc (75 mL)
- washthe combined organic extracts were washed with water (3×50 mL) and brine (50 mL)
- customdried
- customevaporated in vacuo
- customThe residue was recrystallized from DCM
Quellen und Nachweise
- ORD-Eintrag
- ord-7b22dc1deb2b434bab6d460d4a591949
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09024041B2
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