Water → 8-(2,4-Dichlorophenyl)-4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-2-methylquinoline

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Reaction Steps

Under a nitrogen atmosphere, 8-bromo-4-(1,4-dioxa-8-azaspiro [4.5]dec-8-yl)-2-methylquinoline (10.2 g), 2,4-dichlorophenylboric acid (6.0 g) and sodium carbonate (8.93 g) were suspended in a mixed solvent of deaerated water (24 mL), toluene (12 mL) and ethanol (12 mL), followed by adding thereto tetrakis-(triphenylphosphine) palladium (1.6 g), and the resulting mixture was heated under reflux for 16 hours. The reaction mixture was cooled to room temperature and separated with ethyl acetate and a saturated aqueous ammonium chloride solution. After the aqueous phase was extracted with ethyl acetate, the combined organic phase was dried over anhydrous sodium sulfate. The desiccating agent was filtered off, after which the filtrate was concentrated under reduced pressure and the resultant residue was crystallized from diisopropyl ether. The crystals were collected by filtration and washed with a small amount of diisopropyl ether to obtain the title compound (10.5 g).

Provenance & Evidence