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methyl 5-(5-fluoro-2-methoxypyridin-4-yl)-6-methylpyrazine-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In tetrahydrofuran; water; at 100℃; for 1.75h;Inert atmosphere; Reflux;
Step 1: methyl 5-(5-fluoro-2-methoxypyridin-4-yl)-6-methylpyrazine-2-carboxylate To a nitrogen-purged solution of <strong>[77168-85-5]methyl 5-chloro-6-methylpyrazine-2-carboxylate</strong> (15 g, 80 mmol), (5-fluoro-2-methoxypyridin-4-yl)boronic acid (16.49 g, 96 mmol), Pd (dppf) Cl2 dichloromethane adduct (1.2 g,1.469 mmol) and Pd(dppf)C12 (4.6 g, 6.29 mmol) in THF (199 ml) and water (40.8 ml) was addedpotassium phosphate tribasic (51.2 g, 241 mmol) under a nitrogen atmosphere. A reflux condenserwas attached and the mixture was vigorously refluxed with a 100 °C oil bath with stirring. After 105mm, the reaction was cooled to rt and partitioned between EtOAc (200 mL) and water (200 mL).The layers were separated and the aqueous layer was extracted with ethyl acetate (150 mL). Theorganic layers were combined, filtered through C eliteTM, washed with brine, dried over anhydrousMg504, filtered and evaporated to afford a crude residue. The resulting residue was purified via column chromatography on silica gel (ISCO RediSep Gold 330g silica gel column, gradient elution with 0percent to 50percent EtOAc in hexanes) to give the title compound.
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