反応 #45800

反応方程式

phenylboronic acid

tripotassium phosphate

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

→

compound

収率 92.1%

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

収率 92.1%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度this was cooled to room temperature
2. 2
   その他The insoluble matter was separated by filtration
3. 3
   洗浄with washing with ethyl acetate
4. 4
   洗浄The organic layer was washed with saturated brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   その他The solvent was evaporated away
7. 7
   その他the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=3:1)

実験手順

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.

出典