반응 #42868

반응 방정식

4-[2-(4-iodo-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

4-fluorophenylboronic acid

cesium carbonate

→

title compound

수율 124.3%

4-[2-(4′-Fluoro-biphenyl-4-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

수율 124.3%

용매

ethyl acetate

tetrahydrofuran

water

반응 조건

후처리

1. 1
   기타The solution was then degassed
2. 2
   기타by bubbling a flux of argon for 20 minutes
3. 3
   온도to cool down to room temperature
4. 4
   여과The reaction mixture was then filtered
5. 5
   세척the filtrate was then washed twice with brine
6. 6
   건조dried over sodium sulfate
7. 7
   농축before being concentrated in vacuo
8. 8
   여과The residue was then filtered through a pad of silica (SiO2, EtOAc, 100%)

실험 절차

To a solution of 4-[2-(4-iodo-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (0.1 g, 0.428 mmol) in a mixture of tetrahydrofuran (21 mL) and water (5 mL) was added 4-fluorophenylboronic acid (40.3 mg, 0.288 mmol) and cesium carbonate (313 mg, 0.96 mmol). The solution was then degassed by bubbling a flux of argon for 20 minutes before adding polymer bound tetrakis(triphenylphosphine)palladium (Aldrich-511579, 12.86 mg, 0.009 mmol). The reaction mixture was then stirred for 90 min at 80° C. under argon atmosphere before allowing to cool down to room temperature and diluting with ethyl acetate. The reaction mixture was then filtered; the filtrate was then washed twice with brine and dried over sodium sulfate before being concentrated in vacuo. The residue was then filtered through a pad of silica (SiO2, EtOAc, 100%) to yield the title compound as a light brown solid (138 mg, 99%).

출처