4-Aminophenol → 4-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine

HRID 503524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503524
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:16]1[CH:17]=[CH:18][N:19]=[C:20]2[C:25]=1[N:24]=[CH:23][C:22]([O:26][CH3:27])=[CH:21]2.O>CN(C=O)C>[CH3:27][O:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([O:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)=[CH:17][CH:18]=[N:19]2)=[N:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 4034-AminophenolHCID 962WaterHCID 10796Cesium carbonateHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Produkt 1

HCID 441851064-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Five 20 mL microwave vials were each charged with 4-aminophenol (0.700 mg, 33 mmol) and 3 equivalents of cesium carbonate in 6.0 ml of DMF. The mixture was stirred at RT for 10 minutes. Following addition of 8-chloro-3-methoxy-1,5-naphthyridine (1 g, 26 mmol), the reaction vessels were capped and irradiated at 150° C. for 15 min in the microwave, at which time the reaction was determined complete by LCMS. The mixture was allowed to cool to ambient temperature and material from the five vessels was combined. A deep brown solid crashed out with addition of water. Filtered solids, washed with water and dried overnight in the vacuum oven to afford 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine as a brown solid.

Aufarbeitung

  1. customthe reaction vessels
  2. customwere capped
  3. customirradiated at 150° C. for 15 min in the microwave, at which time the reaction
  4. temperatureto cool to ambient temperature
  5. filtrationFiltered solids
  6. washwashed with water
  7. customdried overnight in the vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-cd70aa3c42fc41999055d438f1182d14
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776857B2

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