Hydrogen Peroxide → 2-(Ethylamino)-4-(8-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-2-(trifluoromethyl)quinolin-4-yl)benzamide

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Reaction Steps

Pd(PPh3)4 (0.011 g) was added to a solution of compound (3b) (0.07 g), 4-cyano-3-(ethylamino)phenylboronic acid pinacol ester (0.065 g), and an aqueous sodium carbonate solution (2 M, 1.5 mL) in ethylene glycol dimethyl ether (3.0 mL) in a nitrogen atmosphere, and the mixture was stirred at 85° C. for 3 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was used in the next reaction. An aqueous sodium hydroxide solution (4 M, 0.093 mL) and a 30% aqueous hydrogen peroxide solution (0.045 mL) were added to a solution of the obtained residue in DMSO (3 mL) and ethanol (1.5 mL) at room temperature, and the mixture was stirred for 30 minutes. Water was added to the reaction solution, and the deposit was collected by filtration, then washed with water and ether by sprinkling, and then dried under reduced pressure to obtain compound (3) (0.061 g, yield based on 2 steps: 65%) as a pale yellow solid.

Provenance & Evidence