Reaktion #42874

Reaktionsgleichung

4-[2-(5-bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

2-methoxyphenylboronic acid

cesium carbonate

→

title compound

Ausbeute 79.0%

4-[2-[5-(2-Methoxy-phenyl)-pyridin-2-yloxy]-acetylamino]-thiophene-3-carboxylic acid methyl ester

Ausbeute 79.0%

Lösungsmittel

ethyl acetate

tetrahydrofuran

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution was then degassed
2. 2
   Sonstigeby bubbling a flux of argon for 20 minutes
3. 3
   Temperaturto cool down to room temperature
4. 4
   FiltrationThe reaction mixture was then filtered
5. 5
   Waschenthe filtrate was then washed twice with water
6. 6
   Trocknendried over sodium sulfate
7. 7
   Einengenbefore being concentrated in vacuo
8. 8
   SonstigeThe residue was then purified by column chromatography (SiO2, EtOAc/Heptane, 0-60%)

Vorschrift

To a solution of 4-[2-(5-bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (50 g, 0.135 mmol) in a mixture of tetrahydrofuran (10.5 mL) and water (2.5 mL) was added 2-methoxyphenylboronic acid (24.5 mg, 0.162 mmol) and cesium carbonate (175.3 mg, 0.54 mmol). The solution was then degassed by bubbling a flux of argon for 20 minutes before adding tetrakis(triphenylphosphine)palladium (4.24 mg, 0.0034 mmol). The reaction mixture was then stirred overnight 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 water and dried over sodium sulfate before being concentrated in vacuo. The residue was then purified by column chromatography (SiO2, EtOAc/Heptane, 0-60%) to yield the title compound as a light yellow solid (42.5 mg, 79%).

Quelle