Reaktion #170355

Reaktionsgleichung

5-bromo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide

trimethylboroxine

sodium carbonate

→

title compound

Ausbeute 50.8%

5-Methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide

Ausbeute 50.8%

Lösungsmittel

1,2-dimethoxyethane

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was then irradiated in the microwave for 20 min at 140° C. under an argon atmosphere
2. 2
   Waschenwashed with water (10 mL) and brine (10 mL)
3. 3
   ExtraktionThe aqueous layers were extracted with ethyl acetate (10 mL)
4. 4
   Trocknenthe combined organic layers were dried over sodium sulfate

Vorschrift

To a suspension of 5-bromo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide (200 mg, 0.42 mmol) in 1,2-dimethoxyethane (1 mL) was added trimethylboroxine (88 μL, 0.64 mmol), aqueous sodium carbonate (1 M, 0.64 mL, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (49 mg, 0.04 mmol). The reaction mixture was then irradiated in the microwave for 20 min at 140° C. under an argon atmosphere. It was diluted with ethyl acetate (10 mL) and washed with water (10 mL) and brine (10 mL). The aqueous layers were extracted with ethyl acetate (10 mL) and the combined organic layers were dried over sodium sulfate. Trituration from tert-butylmethylether afforded the title compound (87 mg, 50%) which was obtained as a white solid. MS: m/e=408.4 [M+H]+

Quelle