Dimethylformamide → 4-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid

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Reaction Conditions

Reaction Steps

In a 20 mL microwave tube is added N-(2-bromo-5-chloro-phenyl)-3-chloro-benzamide (0.500 g, 1.45 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.532 g, 1.74 mmol), bis(triphenylphosphine) palladium(II) chloride (0.102 g, 0.145 mmol), 2N Na2CO3 aqueous solution (3.62 mL, 7.25 mmol) and DMF (10 mL). The resulting mixture is placed in a microwave oven and heated to 100° C. for 30 min. The reaction turns black. The reaction mixture is poured into water (30 mL) and filtered. The cake is washed with 10 mL water and air dried. The cake is then dissolved in minimum dichloromethane and purified via flash chromatography using 0-30% EtOAc/hexane. The compound comes at 30% EtOAc. Removal of the solvent under vacuum gives 0.504 g of 4-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tent-butyl ester in 78% yield.

Provenance & Evidence