Triethylamine → Ethyl 7-hydroxy-1,5-naphthyridine-3-carboxylate

HRID 513927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513927
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=[N:16]2)=[N:11][CH:10]=1)C1C=CC=CC=1.C(OC1C=NC2C(C=1)=NC=C(Br)C=2)C1C=CC=CC=1.CCN(CC)CC>CCO.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=[N:16]2)=[N:11][CH:10]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 904173103-(Benzyloxy)-7-bromo-1,5-naphthyridineHCID 90417541Ethyl 7-(benzyloxy)-1,5-naphthyridine-3-carboxylate

Produkt 1

HCID 136227102Ethyl 7-hydroxy-1,5-naphthyridine-3-carboxylateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 498840Bis(benzonitrile)palladium chlorideKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Ethyl 7-(benzyloxy)-1,5-naphthyridine-3-carboxylate. A mixture of 3-(benzyloxy)-7-bromo-1,5-naphthyridine (30.0 g, 95.5 mmol), Et3N (19.47 g, 193 mmol), Pd(PhCN)2Cl2 (1.2 g, 3.13 mmol) and dppf (5.28 g, 9.5 mmol) in EtOH (500 mL) was pressurized to 15 bars with CO gas. Then the mixture was heated at 140° C. for 24 h. After cooling to ambient temperature, the solvent was removed under reduced pressure. Purification (FCC, SiO2, DCM/EtOAc, 1:1) afforded the title compound as a yellow solid (14 g, 67%). [M+H]=309.3.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe solvent was removed under reduced pressure
  3. customPurification (FCC, SiO2, DCM/EtOAc, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ead6abf89fb24054913bcae122344102
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102674B2

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