Reaktion #60541

Reaktionsgleichung

sodium carbonate

5-fluoro-2-methoxyphenylboronic acid

4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

1,2-dimethoxyethane

→

title compound

Ausbeute 127.3%

4-(5-Fluoro-2-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

Ausbeute 127.3%

Lösungsmittel

Brine

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
2. 2
   Einengenthe filtrate was concentrated
3. 3
   Sonstigeto give a residue, which
4. 4
   Sonstigewas purified by silica gel column chromatography (ethyl acetate/heptane)

Vorschrift

To a mixture of 5-fluoro-2-methoxyphenylboronic acid (1 g, 5.88 mmol), 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (4.22 g, 7.64 mmol) (David J. Wustrow, Lawrence D. Wise, Synthesis, 1991, 993) and 1,2-dimethoxyethane (30 mL) were added tetrakis(triphenylphosphine)palladium(0) (0.34 g, 0.29 mmol) and 2N aqueous solution of sodium carbonate (8.82 mL, 17.6 mmol), followed by stirring for 2 hours at an external temperature of 90° C. under a nitrogen atmosphere. Brine was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the filtrate was concentrated to give a residue, which was purified by silica gel column chromatography (ethyl acetate/heptane) to give 2.3 g of the title compound as a yellow oil.

Quelle