반응 #45800

반응 방정식

phenylboronic acid

tripotassium phosphate

Methyl 3-amino-5-bromo-4-fluoro-2-methoxybenzoate

→

compound

수율 92.1%

Methyl 5-amino-6-fluoro-4-methoxybiphenyl-3-carboxylate

수율 92.1%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도this was cooled to room temperature
2. 2
   기타The insoluble matter was separated by filtration
3. 3
   세척with washing with ethyl acetate
4. 4
   세척The organic layer was washed with saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타The solvent was evaporated away
7. 7
   기타the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=3:1)

실험 절차

Methyl 3-amino-5-bromo-4-fluoro-2-methoxybenzoate (I-230) (504 mg, 1.81 mmol) was dissolved in 1,4-dioxane (10 ml), then under nitrogen atmosphere at room temperature, phenylboronic acid (456 mg, 3.62 mmol), tripotassium phosphate (770 mg, 3.62 mmol) and tetrakis(triphenylphosphine)palladium(0) (210 mg, 0.18 mmol) were added. After stirred at 90° C. for 36 hours, this was cooled to room temperature. The insoluble matter was separated by filtration with washing with ethyl acetate, the filtrate was fractionated with ethyl acetate and saturated brine. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=3:1) to obtain the entitled compound (459 mg, 92%) as a colorless gel substance.

출처