Nitrogen → 5-iodo-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole

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Reaction Steps

To a round-bottomed flask equipped with a stirring bar and a N2 tee, tetrahydro-2H-pyran-4-ol (1.05 g, 10.31 mmol), 5-iodo-1H-pyrazole (2.00 g, 10.31 mmol), triphenylphosphine (3.33 g, 12.68 mmol), (g, mmol) and THF (22.9 mL) were added. Followed by the addition of DIAD (2.71 g, 13.4 mmol), the resulting mixture was stirred at room temperature for 3 hrs. The mixture was removed most solvents in vauo, and ethyl acetate (200 mL) was added. The resulting solution were washed with H2O (50 mL×1), brine (50 mL×1), and dried over Na2SO4. The organic phase was filtered and removed solvent in vacuo, and passed a silica gel column (ethyl acetate: hexanes=0:100 to 100:0), off-white solids were obtained as the desired product. 920 mg (yield 32.1%). 1H NMR (300 MHz, DMSO-d6) δ 7.63-7.47 (m, 1H), 6.62-6.38 (m, 1H), 4.48 (tt, J=11.4, 4.3 Hz, 1H), 3.96 (ddt, J=11.8, 4.7, 1.2 Hz, 2H), 3.49 (td, J=12.0, 2.1 Hz, 2H), 2.00 (dddd, J=13.1, 12.0, 11.2, 4.6 Hz, 2H), 1.90-1.71 (m, 2H) ppm; MS (ESI+) m/z 279.30 (M+H).

Provenance & Evidence