Sodium hydride → 4-[3,3-Dimethyl-6-(Morpholin-4-Yl)-2,3-Dihydro-1h-Indol-1-Yl]-7-Fluoro-3-Methyl-2-(Pyridin-3-Yl)quinoline

HRID 1618492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618492
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:3]=1[CH3:19].[CH3:20][C:21]1([CH3:36])[C:29]2[C:24](=[CH:25][C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:27][CH:28]=2)[NH:23][CH2:22]1.[H-].[Na+]>CN(C=O)C>[CH3:20][C:21]1([CH3:36])[C:29]2[C:24](=[CH:25][C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:27][CH:28]=2)[N:23]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=3)[N:5]=[C:4]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[C:3]=2[CH3:19])[CH2:22]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 596310524-Chloro-7-fluoro-3-methyl-2-(pyridin-3-yl)quinolineHCID 672848583,3-Dimethyl-6-morpholinoindoline

Produkt 1

HCID 509392094-[3,3-Dimethyl-6-(Morpholin-4-Yl)-2,3-Dihydro-1h-Indol-1-Yl]-7-Fluoro-3-Methyl-2-(Pyridin-3-Yl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Prepared according to procedure M using 4-chloro-7-fluoro-3-methyl-2-(pyridin-3-yl)quinoline (250 mg, 0.92 mmol), 4-(3,3-dimethylindolin-6-yl)morpholine (213 mg, 0.92 mmol) and sodium hydride (44 mg, 1.833 mmol) in DMF (2.0 mL) and heating the reaction at 120° C. for 3 h. After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-3-methyl-2-(3-pyridinyl)-quinoline was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.90 (1H, br. s.), 8.66-8.81 (1H, m), 8.00 (1H, dt, J=7.8, 2.0 Hz), 7.89 (1H, dd, J=9.4, 5.9 Hz), 7.81 (1H, dd, J=10.0, 2.5 Hz), 7.48 (1H, dd, J=7.8, 4.7 Hz), 7.23-7.30 (1H, m), 7.09 (1H, d, J=8.2 Hz), 6.34 (1H, dd, J=8.2, 2.3 Hz), 5.61 (1H, d, J=2.3 Hz), 3.68-3.81 (6H, m), 2.90-3.02 (4H, m), 2.30 (3H, s), 1.52 (3H, s), 1.47 (3H, s). Mass Spectrum (ESI) m/e=469 (M+1).

Aufarbeitung

  1. customPrepared
  2. temperatureheating
  3. customthe reaction at 120° C. for 3 h
  4. customAfter purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-3-methyl-2-(3-pyridinyl)-quinoline
  5. customwas obtained as a yellow film

Quellen und Nachweise

ORD-Eintrag
ord-db74d4db00274dbd93d1d61b2626ca9a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765940B2

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