تفاعل #60541

معادلة التفاعل

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

المردود 127.3%

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

المردود 127.3%

المذيبات

Brine

ethyl acetate

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر