Potassium Carbonate → tert-Butyl (1-pyridazin-3-ylpiperidin-4-yl)carbamate

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The reaction mixture of tert-butyl piperidin-4-ylcarbamate (250 mg, 1.25 mmol), 3-bromopyridazine (258 mg, 1.62 mmol), CsF (37.9 mg, 0.25 mmol), and K2CO3 (518 mg, 3.74 mmol) in DMSO (12.5 mL) was heated at 100° C. for 20 h. Water and DCM were poured into the mixture, and the separated aqueous layer was extracted with DCM, the combined organic layers were dried over Na2SO4, filtered, concentrated in vacuo. The residue was purified by column chromatography (Hexane:EtOAc=1:1) to give tert-butyl 1-(pyridazine-3-yl)piperidin-4-ylcarbamate (123 mg, 35%) as a pale yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 1.45 (9H, s), 1.92-2.12 (2H, m), 3.03-3.17 (2H, m), 3.55-3.80 (2H, m), 4.25-4.38 (2H, m), 4.52 (1H, brs), 6.92 (1H, d, J=9.2 Hz), 7.20 (1H, dd, J=4.4, 9.2 Hz), 8.56 (1H, d, J=4.4 Hz). NH peak was not observed. m/z=279.06 [M+1]+.

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