반응 #634130

반응 방정식

2-[4-(1-{4-[(E)-3-(t-butyl-dimethyl-silanyloxy)-4,4,4-trifluoro-3-trifluoromethyl-1-butenyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-bromopyrimidine-5-acetic acid ethyl ester

potassium phosphate

→

title compound

수율 41.0%

[2-(4-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2-methyl-phenyl)-pyrimidin-5-yl]-acetic Acid Ethyl Ester

수율 41.0%

용매

Water

반응 조건

후처리

1. 1
   기타Degassed N,N-dimethylformamide (0.32 mL)
2. 2
   온도After replacement with nitrogen, the mixture was heated
3. 3
   추출followed by extraction with diethyl ether
4. 4
   건조The extract was dried over anhydrous magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1)

실험 절차

Degassed N,N-dimethylformamide (0.32 mL) was added to 2-[4-(1-{4-[(E)-3-(t-butyl-dimethyl-silanyloxy)-4,4,4-trifluoro-3-trifluoromethyl-1-butenyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 77-(1); 35.8 mg, 0.0523 mmol), 2-bromopyrimidine-5-acetic acid ethyl ester (Example 43-(3); 37.3 mg, 0.152 mmol), tetrakis(triphenylphosphine)palladium (0) (29.8 mg, 0.0258 mmol) and potassium phosphate (48.7 mg, 0.229 mmol). After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 91 to 100° C. for 10 hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=4/1) to give the title compound (13 mg, 41%).

출처