Reaktion #448634

Reaktionsgleichung

sodium carbonate

1,4-benzenediboronic acid

2-chloropyrimidine

2-chloro-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

→

N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-[pyrimidin-2-yl]phenyl)pyridine-3-sulphonamide

Ausbeute 17.9%

Lösungsmittel

Water

water

toluene

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated under argon
2. 2
   Temperaturunder reflux for 16 hours
3. 3
   Extraktionthe mixture was extracted with ethyl acetate (2×20 ml)
4. 4
   WaschenThe combined organic layers were washed with saturated sodium chloride solution
5. 5
   Trocknendried (MgSO4)
6. 6
   SonstigeVolatile material was removed by evaporation
7. 7
   Sonstigethe residue was purified by chromatography on a silica gel Mega Bond Elut column
8. 8
   Wascheneluting with 25-100% ethyl acetate/hexane

Vorschrift

Tetrakis(triphenylphosphine)palladium (0) (60 mg) was added to a deoxygenated solution of sodium carbonate (233 mg), 1,4-benzenediboronic acid (165 mg), 2-chloropyrimidine (114.5 mg) and 2-chloro-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (414 mg) in a mixture of water (1.6 ml), ethanol (4 ml) and toluene (8 ml). The mixture was stirred and heated under argon under reflux for 16 hours and then allowed to cool to ambient temperature. Water (15 ml) was added and the mixture was extracted with ethyl acetate (2×20 ml). The combined organic layers were washed with saturated sodium chloride solution and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column, eluting with 25-100% ethyl acetate/hexane to give N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-[pyrimidin-2-yl]phenyl)pyridine-3-sulphonamide (95 mg) as a solid, mass spectrum (+ve ESP): 535 (M+H)+.

Quelle