Triethylamine → t-Butyl 4-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-ylcarbamoyl]piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 4-(2-fluoro-4-nitrophenoxy)pyridin-2-ylamine (400 mg, 1.61 mmol) in N,N-dimethylformamide (16 ml) were added Boc-isonipecotic acid (554 mg, 2.42 mmol), triethylamine (0.673 ml, 4.83 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.07 g, 2.42 mmol), followed by stirring at room temperature for 6.5 hrs. Boc-isonipecotic acid (554 mg, 2.42 mmol), triethylamine (0.673 ml, 4.83 mmol), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.07 g, 2.42 mmol) were further added thereto, followed by stirring at room temperature for 3 hrs. Furthermore, Boc-isonipecotic acid (554 mg, 2.42 mmol), triethylamine (0.673 ml, 4.83 mmol), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.07 g, 2.42 mmol) were added thereto, followed by stirring at room temperature for 3 days. To the reaction mixture was added ethyl acetate (150 ml), washed with a saturated aqueous solution of sodium hydrogencarbonate, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then subjected to silica gel column chromatography (Fuji Silysia NH, eluent; hexane:ethyl acetate=1:1, then ethyl acetate) to provide a crude product of the titled compound (548 mg) as a yellow oil.

Provenance & Evidence