Reaktion #168663

Reaktionsgleichung

Na2CO3

DCM

DCM

5-bromo-2,4-difluoro-N-(4-hydroxy-cyclohexyl)-benzenesulfonamide

BIS(pinacolato)diboron

3-amino-6-bromo-pyrazine-2-carboxylic acid methoxy-methyl-amide

→

titled compound

2-Amino-5-[2,4-difluoro-5-(4-hydroxy-cyclohexylsulfamoyl)-phenyl]-N-methoxy-N-methyl-nicotinamide

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 4 hours
2. 2
   TemperaturThe reaction mixture is refluxed for 30 minutes
3. 3
   SonstigeThe crude reaction mixture
4. 4
   Sonstigeis purified by normal phase chromatography (30-100% EtOAc/iso-hexane)

Vorschrift

A suspension of 5-bromo-2,4-difluoro-N-(4-hydroxy-cyclohexyl)-benzenesulfonamide—intermediate DX (300 mg, 0.81 mmol), BIS(pinacolato)diboron (222 mg, 0.88 mmol) and Pd(dppf)Cl2.DCM (0.066 g, 0.08 mmol) in DME (12 ml) is heated at reflux for 4 hours. 2M Na2CO3 (4 ml) is added to the reaction mixture followed by 3-amino-6-bromo-pyrazine-2-carboxylic acid methoxy-methyl-amide (0.211 g, 0.81 mmol) and Pd(dppf)Cl2.DCM (0.066 g, 0.08 mmol). The reaction mixture is refluxed for 30 minutes. The crude reaction mixture is purified by normal phase chromatography (30-100% EtOAc/iso-hexane) to afford a white solid as the titled compound. [M+H]+ 472

Quelle