Reaktion #74172

Reaktionsgleichung

sodium carbonate

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

N-{3-[4-bromo-1-(2-methylpropyl)-1H-pyrazol-3-yl]-2,4-difluorophenyl}-2,5-difluorobenzenesulfonamide

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

→

title compound

N-[3-(1-i-butyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamide

Lösungsmittel

dimethoxyethane

dimethoxyethane

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe mixture was insufflated with nitrogen for 10 min
2. 2
   workup.WAITthe process was resumed for 0.5 h
3. 3
   TemperaturThe mixture was cooled
4. 4
   Einengenthe organic phase was concentrated
5. 5
   SonstigeThe crude oil was purified by flash chromatography (eluant: dichloromethane/methanol 30:1)

Vorschrift

To a solution of tetrakis(triphenylphosphine)palladium(0) (0.035 g, 0.03 mmol) in dimethoxyethane (1 mL), N-{3-[4-bromo-1-(2-methylpropyl)-1H-pyrazol-3-yl]-2,4-difluorophenyl}-2,5-difluorobenzenesulfonamide (0.09 g, 0.18 mmol) in dimethoxyethane (1 mL) was added and the mixture was insufflated with nitrogen for 5 min. A solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.08 g, 0.4 mmol)) in dimethoxyethane (1 mL) was added and the mixture was insufflated with nitrogen for 10 min, then 2 M sodium carbonate solution (1 mL) was added and the mixture was heated at 110° C. in a microwave cavity for 1 h. More tetrakis(triphenylphosphine)palladium(0) (0.012 g, 0.01 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.016 g, 0.08 mmol) were added and the process was resumed for 0.5 h. The mixture was cooled and the organic phase was concentrated. The crude oil was purified by flash chromatography (eluant: dichloromethane/methanol 30:1). The title compound was obtained as a white solid (0.025 g, 28%).

Quelle