Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → tert-butyl 2-(3-(4-methylphenylsulfonamido)cyclobutoxy)-5',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(3-((3-bromopyridin-2-yl)oxy)cyclobutyl)-4-methylbenzenesulfonamide (397 mg, 1 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (335 mg, 1.1 mmol) and NaCO3 (212 mg, 2 mmol) in 1,4-dioxane (60 mL) and H2O (6 mL) was added Pd(dppf)Cl2 (36.6 mg, 0.05 mmol). The reaction mixture was stirred at 110° C. under N2 overnight. The reaction mixture was filtered through CELITE® and washed with CH2Cl2. The organic layer was concentrated and the crude product was purified by silica gel column to give tert-butyl 2-(3-(4-methylphenylsulfonamido)cyclobutoxy)-5′,6′-dihydro-[3,4′-bipyridine]-1′(2′H)-carboxylate (351 mg, 0.7 mmol, yield 70%). ESI-MS (M+1): 500 calc. for C26H33N3O5S 499.

Provenance & Evidence