تفاعل #75570

معادلة التفاعل

1-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine

4-methoxyphenylboric acid

toluene

sodium carbonate

→

title compound

المردود 39.1%

4-(3-Chloro-4-methoxybenzyl)amino-6-cyano-1-(4-methoxyphenyl)phthalazine hydrochloride

المردود 39.1%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.WAITfurther at 10° C. for 15.5 hr
2. 2
   أخرىwas returned to room temperature
3. 3
   استخلاصextracted with aqueous ammonium chloride and ethyl acetate
4. 4
   غسيلThe organic layer was washed with aqueous ammonia, water and brine
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   أخرىThe solvent was evaporated
7. 7
   أخرىthe resulting residue was purified by silica gel column chromatography
8. 8
   workup.DISSOLUTIONwas dissolved in ethyl acetate/ethanol
9. 9
   workup.ADDITION4 N hydrochloric acid/ethyl acetate solution was added
10. 10
    ترشيحthe resulting crystals were collected by filtration

الإجراء التجريبي

423 mg of tetrakis(triphenylphosphine)palladium (0) was added to a mixture of 1.0 g 1-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine, 423 mg 4-methoxyphenylboric acid, 30 ml toluene, 30 ml tetrahydrofuran, and 30 ml of 2 M aqueous sodium carbonate in a nitrogen atmosphere. The mixture was stirred at 80° C. for 2 hr, and further at 10° C. for 15.5 hr. The reaction solution was returned to room temperature and extracted with aqueous ammonium chloride and ethyl acetate. The organic layer was washed with aqueous ammonia, water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography. The resulting coupled compound was dissolved in ethyl acetate/ethanol, 4 N hydrochloric acid/ethyl acetate solution was added thereto, and the resulting crystals were collected by filtration to give 460 mg of the title compound as a yellow powder.

المصدر