Potassium Carbonate → 5-(2-cyclopropylethylcarbamoyl)-3',6'-dihydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-chloronicotinic acid (2-cyclopropylethyl)amide (0.650 g, 2.893 mmol) in DMF (15 mL) was added 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.075 g, 3.479 mmol), potassium carbonate (1.202 g, 8.697 mmol) and tetrakis(triphenylphosphine)palladium (0.347 g, 0.300 mmol). The resulting mixture was heated to 80° C. for 24 hours and then filtered. Ethyl acetate (40.0 mL) was added to the mixture and the organic solution was washed with water (20 mL), saturated NaCl (20 mL), dried over MgSO4 and then concentrated in vacuo. The crude product was purified by column chromatography to yield the desired product, 5-(2-cyclopropylethylcarbamoyl)-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (0.453 g, 42%).

Provenance & Evidence