3-CHLORO-4-(TRIFLUOROMETHOXY)BENZALDEHYDE

Diisobutylaluminum hydride (1.0 M in toluene, 28 mL, 28 mmol) was added slowly via syringe to a solution of 3-chloro-4-(trifluoromethyl)benzonitrile (3.79 g, 18.4 mmol) in THF (50 mL) at 0° C. Hydrazine-1-methyl-1-hydro-pyrazolo [3, 4-d] pyrimidine (100 mg, 609ymol) In a 25 mL single-neck flask, 10 mL of absolute ethanol was taken and 50 mg of acetic acid was added dropwise. The mixture was heated and stirred until the starting material was completely dissolved. To the above reaction system was added 3-chloro-4- trifluoromethylbenzaldehyde (254 mg, 1.2 mmol) , And the mixture was heated to reflux for 2.5h, then cooled to room temperature, filtered, the filter cake was washed with absolute ethanol, and recrystallized from anhydrous ethanol to obtain 200mg of a white solid with a yield of 92percent.To a solution of 13 (550 mg, 2.226 mmol) in toluene 25 mL was added