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

HRID 2212591

Reaction equation

[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].I[CH2:19][CH2:20][CH3:21].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[CH2:19][CH2:20][CH3:21])=[CH:6][C:5]=1[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of powdered potassium hydroxide (1.26 g, 22.38 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) (3.0 g, 11.19 mmol) was added cautiously, followed immediately by the addition of 1-iodopropane (5.5 mL, 55.95 mmol). The reaction mixture was 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 (MgSO4), filtered and evaporated to give 4.0 g of 7-bromo-1-propyl-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one and used without further purification in the Suzuki coupling (step a). 1H NMR (300 MHz; CDCl3): 0.98 (t, J=7.5 Hz,1 H), 1.26 (s, 6 H), 1.65 (t, J=7.5 Hz, 1 H), 2.37 (s, 3 H), 2.46 (s, 2 H), 3.88 (t, J=7.8 Hz, 2 H), 7.13 (s, 1 H), 7.15 (s, 1 H).

Workup

temperatureThe reaction mixture was warmed up to room temperature
stirringstirred overnight at room temperature
extractionextracted with dichloromethane
washwashed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-19f8755c4259480d81d941cfea1486da
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07102000B2

Linked notes

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