반응 #45572

반응 방정식

water

N,N-dimethylformamide

N-(2-cyano-5-fluoro-4-iodo-6-methoxy-3-methylphenyl)-2,2,2-trifluoroacetamide

phenylboronic acid

→

compound

수율 98.0%

N-(5-Cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2,2-trifluoroacetamide

수율 98.0%

용매

brine

반응 조건

후처리

1. 1
   온도with heating
2. 2
   온도under reflux for 15 hours
3. 3
   추출followed by extraction three times with ethyl acetate
4. 4
   세척the organic layer was washed with saturated ammonium chloride water
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   여과After filtration and concentration under reduced pressure
7. 7
   농축the eluate with n-hexane:ethyl acetate (5:1) was concentrated under reduced pressure

실험 절차

Under nitrogen atmosphere, tetrakistriphenylphosphine palladium(0) (288 mg, 0.25 mmol) was added to an N,N-dimethylformamide (15 ml) suspension of N-(2-cyano-5-fluoro-4-iodo-6-methoxy-3-methylphenyl)-2,2,2-trifluoroacetamide (I-35) (500 mg, 1.24 mmol), phenylboronic acid (228 mg, 1.87 mmol), potassium phosphate n-hydrate (890 mg, 3.1 mmol), followed by stirring with heating under reflux for 15 hours and a half. After cooling to room temperature, water and saturated brine were added to the reaction liquid, followed by extraction three times with ethyl acetate, the organic layer was washed with saturated ammonium chloride water, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (5:1) was concentrated under reduced pressure to obtain the entitled compound (427 mg, 98%) as a white solid.

출처