Water → 7-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one

HRID 1790199

Reaktionsgleichung

[OH-].[K+].[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH3:16])([CH3:15])[CH2:9][C:10](=[O:14])[NH:11]2)=[CH:6][C:5]=1[CH3:17].[CH2:18](I)C.O>CS(C)=O>[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH3:15])([CH3:16])[CH2:9][C:10](=[O:14])[N:11]2[CH3:18])=[CH:6][C:5]=1[CH3:17]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A mixture of powdered potassium hydroxide (3.35 g, 59.67 mmol) in DMSO (40 mL) was stirred at 0° C. for 10 min. 7-bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one (Example 1e) (8.0 g, 29.83 mmol) was added cautiously, followed immediately by the addition of ethyl iodide (12 mL, 149.17 mmol). The reaction mixture was kept at 0° C. for 30 min then slowly warmed up to room temperature and stirred overnight at room temperature. The reaction mixture was poured into water and extracted with dichloromethane washed with water and brine, dried (Mg2SO4), filtered and evaporated to give 8.8 g of 7-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one and used without further purification in the Suzuki coupling (step a). 1H NMR (300 MHz; CDCl3): 1.24 (t, J=7.2 Hz, 1 H), 1.25 (s, 6 H), 2.37 (s, 3 H), 2.45 (s, 2 H), 3.98 (q, 2 H), 7.13 (s, 1 H), 7.18 (s, 1 H).

Aufarbeitung

waitThe reaction mixture was kept at 0° C. for 30 min
temperaturethen slowly warmed up to room temperature
stirringstirred overnight at room temperature
extractionextracted with dichloromethane
washwashed with water and brine
dry with materialdried (Mg2SO4)
filtrationfiltered
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-77caa91568234d24a077c16a3f1fb4fb
Quelldatensatz: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07071218B2

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