Lithium Hydroxide → HCID 67036415, Verbindung

HRID 1623479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1623479
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH3:21])[C:12]2=[O:29])[CH:5]=1.[OH-].[Li+]>C1COCC1.O>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:20](=[C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:30])=[O:2])[C:12]2=[O:29])[CH3:21])=[CH:27][CH:26]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 67036322HCID 67036322, Verbindung

Produkt 1

HCID 67036415HCID 67036415, VerbindungAusbeute 31,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-{3-[1-(4-fluoro-phenyl)-ethylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (0.33 g, 0.82 mmol) was dissolved in THF 5 ml. Then a solution of lithium hydroxide (0.35 g, 8.2 mmol) in water (2.0 ml) was added. After stirring for 12 hours, the solvent was removed under reduced pressure. The residue was dissolved in 2 ml DMF for prepared HPLC to give 3-{3-[1-(4-fluoro-phenyl)-ethylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid as yellow powder (100 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.78 (s, 3H) 5.06 (s, 2H) 6.08 (d, J=7.83 Hz, 1H) 6.68 (t, J=7.45 Hz, 1H) 6.92 (d, J=7.83 Hz, 1H) 7.11 (t, J=7.45 Hz, 1H) 7.38 (t, J=8.84 Hz, 2H) 7.43-7.51 (m, 1H) 7.46 (dd, J=8.72, 5.68 Hz, 2H) 7.60 (d, J=7.58 Hz, 1H) 7.85 (d, J=7.83 Hz, 1H) 7.92 (s, 1H) 13.03 (s, 1H). MS calcd. for C24H18FNO3 387.4, obsd. (ESI+) [(M+H)+] 388.2.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 2 ml DMF
  3. customfor prepared HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0d39b84786324e2a85dcec9ecf80b75c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778973B2

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