Sodium ethoxide → Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

HRID 2364213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2364213
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C:6]([N:8]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[C:9]1[C:10]([C:23]([O:25]CC)=O)=[N:11][CH:12]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:14]=1)=[O:7])[CH3:2].[O-]CC.[Na+]>C(O)C>[F:34][C:31]1[CH:32]=[CH:33][C:28]([N:8]2[C:9]3[C:10](=[N:11][CH:12]=[C:13]([CH2:15][C:16]4[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=4)[CH:14]=3)[C:23]([OH:25])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:35])[C:6]2=[O:7])=[CH:29][CH:30]=1

Komponenten

4

Edukt 2

HCID 2723922Sodium ethoxideHCID 69481480Ethyl 3-[(3-ethoxy-3-oxopropanoyl)(4-fluorophenyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate

Produkt 1

HCID 59799019Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylateAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 3-[(3-ethoxy-3-oxopropanoyl)(4-fluorophenyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate (477 mg, 0.99 mmol) was dissolved in ethanol (50 mL) and sodium ethoxide (0.91 mL of a 2.4 M solution) was added. The solution was stirred until reaction was determined complete by LC-MS and the suspension was concentrated under reduced pressure. A small amount of water was added and the mixture was acidified with 1 N hydrochloric acid to a pH of 3 and the resulting white solid was collected by vacuum filtration to yield ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (368 mg, 85% yield). 1H NMR (methanol-d4/CDCl3) δ 8.19 (s, 1 H), 7.17-7.06 (m, 4 H), 6.94-6.83 (m, 4 H), 6.58 (s, 1 H), 4.26 (q, J=7.2 Hz, 2 H), 3.81 (s, 2 H), 1.27 (t, J=7.2 Hz, 3 H); MS m/z 459 (M+23).

Aufarbeitung

  1. concentrationthe suspension was concentrated under reduced pressure
  2. additionA small amount of water was added
  3. filtrationthe resulting white solid was collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-2bc18f2527ba4463a2dd9ae00317191d
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691991B2

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