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8-(2-methoxy-7-quinolyl)-1,4-dioxa-8-azaspiro[4.5]decane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
900 mg
With sodium t-butanolate; In 1,4-dioxane; at 100.0℃; for 12.0h;Inert atmosphere;
To a solution of 1,4-dioxa-8-azaspiro[4.5]decane (550 mg, 3.06 mmol) and 7-bromo-2- methoxyquinoline (875 mg, 3.67 mmol) in dioxane (5 mL) was added t-BuONa (883 mg, 9.18 mmol) under N2. After being heated with stirring at 100 C for 12 hrs, the resulting reaction mixture was cooled to rt and concentrated in vacuo. The residue was diluted with H20 (60 mL) and extracted with DCM (150 mL). The organic layer was washed with brine (60 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column to give 8- (2-methoxy-7 -quinolyl)- 1 ,4-dioxa-8-azaspiro [4.5] decane (900 mg) as yellow oil.
(E)-N-(2-(2-methoxyquinolin-7-yl)vinyl)isoindoline-1,3-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With palladium diacetate; tris-(o-tolyl)phosphine; In N,N-dimethyl-d6-formamide; at 110.0℃; for 3.0h;Sealed tube; Inert atmosphere;
General procedure: In a sealed tube under argon atmosphere, were introducedcompound 4 (4.74 g, 20 mmol), DMF (20 mL), triethylamine(11.16 mL, 80 mmol), palladium diacetate (225 mg, 1 mmol), tri(otolyl)-phosphine (609 mg, 2 mmol) and N-vinylphthalimide (5.20 g,30 mmol). The mixturewas stirred at 110 C for 3 h and hydrolyzed.The formed solid was solubilized in CH2Cl2, washed with water andbrine, dried over MgSO4 and evaporated under reduced pressure.The crude productwas recrystallized from acetonitrile to afford 7 asa white solid (91% yield)
(E)-ethyl 3-(2-methoxyquinolin-7-yl)prop-2-enoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
93%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In N,N-dimethyl-formamide; at 120.0℃; for 15.0h;Inert atmosphere;
General procedure: To a solution of 2 (30.63 g, 100 mmol) in DMF (150 mL) under an inert atmosphere, were added ethyl acrylate (11.97 mL, 110 mmol), bis(triphenylphosphine) palladium chloride (7.72 g, 11 mmol) and triethylamine (15.29 mL, 110 mmol). The reaction mixture was refluxed at 120 C for 15 h, cooled to room temperature, hydrolyzed with water and then extracted twice with ethyl acetate. The combined organic layers were washed with a 1 M solution of HCl, water and brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography (SiO2, cyclohexane/EtOAc: 7/3) to give 4 (77%) as a white solid.
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