Benzoate → Ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-benzyl-6-quinolinyl)ethynyl]benzoate

HRID 52454

Reaktionsgleichung

Reaktionsgleichung von HRID 52454
[H-].[Na+].[CH3:3][C:4]1([CH3:26])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[C:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([O-:22])=[O:21])=[CH:18][CH:17]=3)[CH:12]=2)[NH:7][C:6](=[O:25])[CH2:5]1.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:35]([O-])(=O)[C:36]1C=CC=CC=1>CN(C=O)C>[CH3:3][C:4]1([CH3:26])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[C:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([O:22][CH2:35][CH3:36])=[O:21])=[CH:18][CH:17]=3)[CH:12]=2)[N:7]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:6](=[O:25])[CH2:5]1

Komponenten

6

Edukt 4

HCID 242BenzoateHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 199637384-[(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolinyl)ethynyl]benzoate2×

Produkt 1

HCID 19963704Ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-benzyl-6-quinolinyl)ethynyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (93.6 mg, 2.6 mmol), ethyl 4-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolinyl) ethynyl benzoate (Compound 4, 604 mg, 1.7 mmol) and benzyl bromide (2.06 mL, 17 mmol) in 3 mL of DMF were reacted substantially in accordance with the procedure used for the preparation of ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-(1-iso-propyl-6-quinolinyl)ethynyl]benzoate (Compound 5), to yield the title compound as white solids (744 mg).

Quellen und Nachweise

ORD-Eintrag
ord-f573eba3c4f04e5d987a05000aaa80d9
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616712

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