Ethanol → (8-Benzyloxy-quinolin-2-yl)[4-(2-methoxy-ethoxy)-2-nitro-phenyl]-amine

Participants

Reaction Conditions

Reaction Steps

8-Benzyloxy-2-chloro-quinoline 77B (25.53 g, 94.64 mMol) was added to 350 mL of anhydrous toluene under an atmosphere of dry N2. To this solution was added 5-(2-methoxyethoxy)-2-nitro-phenylamine 42A (20.08 g, 94.64 mMol), palladium acetate (433 mg, 1.89 mMol), Cs2CO3 (43.2 g, 132 mMol), phenyl boronic acid (584 mg, 4.79 mMol) and 1,2-bis(diphenylphosphino)-ethane (2.33 g, 5.68 mMol) and the mixture was then deoxygenated by bubbling argon through for ten minutes. The reaction mixture was then heated to 95° C. and reacted at this temperature for two hours. Then the reaction was diluted (while still hot) with 350 mL of DCE and then filtered while still hot. The filter cake was washed with 100 mL of hot DCE. The filtrate was concentrated to ˜175 mL during which time a large amount of precipitate formed. To this mixture was added 400 mL of EtOH and the reaction mixture was stirred overnight. The resulting red precipitate was collected via suction filtration and dried under vacuum to give 36.8 g of the title compound as a red solid 77C.

Provenance & Evidence