Dimethylformamide → HCID 86730348, compound

Participants

Reaction Conditions

Reaction Steps

N,N-dimethylformamide (100 mL) was added to commercially available 1-N—BOC-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine (4.68 g, 15.1 mmol), commercially available methyl 6-chloronicotinate (2.81 g, 16.4 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) (1.17 g, 1.60 mmol), and potassium carbonate (7.02 g, 50.8 mmol). The reaction liquid was stirred under nitrogen atmosphere at 100° C. for 2 hours. The reaction liquid was allowed to stand to cool to room temperature and then diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed serially with a dilute aqueous ammonia solution and a saturated saline solution, and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1) to obtain the title compound (1.07 g, 22%).

Provenance & Evidence