반응 #75570

반응 방정식

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

4-methoxyphenylboric acid

toluene

sodium carbonate

→

title compound

수율 39.1%

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

수율 39.1%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.WAITfurther at 10° C. for 15.5 hr
2. 2
   기타was returned to room temperature
3. 3
   추출extracted with aqueous ammonium chloride and ethyl acetate
4. 4
   세척The organic layer was washed with aqueous ammonia, water and brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타The solvent was evaporated
7. 7
   기타the 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
    여과the resulting crystals were collected by filtration

실험 절차

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.

출처