Sodium Carbonate → tert-Butyl 5-chloro-6-methoxy-5',6'-dihydro-[2,4'-bipyridine]-1'(2'H)-carboxylate

To a 1,4-dioxane (50 mL)-water (10 mL) solution of 6-bromo-3-chloro-2-methoxypyridine (1.98 g, 8.90 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.50 g, 8.09 mmol), and sodium carbonate (1.71 g, 16.1 mmol), tetrakis(triphenylphosphine)palladium (0) (467 mg, 0.400 mmol) was added under argon atmosphere and the resultant mixture was stirred at 100° C. for 3 hours. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the title compound (2.55 g, yield 97%).

1. washThe organic layer was washed with brine
2. dry with materialdried over anhydrous sodium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

ORDレコード

ord-cfc8eb8e2fe444c999c84fdcf1138b62

出典データセット

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09403798B2