反応 #425493

反応方程式

5-bromo-6-fluoro-1H-indole

4-methoxyphenyl boronic acid

potassium carbonate

→

title compound

収率 22.0%

6-Fluoro-5-(4-methoxy-phenyl)-1H-indole

収率 22.0%

溶媒

EtOH

toluene

反応条件

後処理

1. 1
   その他were degassed with N2 for 5 minutes
2. 2
   その他degassed for an additional 5 minutes
3. 3
   その他The reaction mixture was sealed
4. 4
   温度The reaction was cooled to room temperature
5. 5
   その他the layers were separated
6. 6
   濃縮The organic layer was concentrated in vacuo
7. 7
   その他the crude material was purified by flash chromatography (25-75% EtOAc/heaptane)

実験手順

A mixture of 5-bromo-6-fluoro-1H-indole (600.0 mg, 2.80 mmol), 4-methoxyphenyl boronic acid (426.0 mg, 2.80 mmol), 2N aqueous potassium carbonate (8.49 mL, 16.98 mmol) in EtOH (8 mL) and toluene (3 mL) were degassed with N2 for 5 minutes, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (180.0 mg, 0.22 mmol), and degassed for an additional 5 minutes. The reaction mixture was sealed and heated to 80° C. for 16 hours. The reaction was cooled to room temperature and the layers were separated. The organic layer was concentrated in vacuo and the crude material was purified by flash chromatography (25-75% EtOAc/heaptane) to give the title compound (147 mg, 22% yield). MS (ES+) 242.3 (M+1)+.

出典