Imidazole → HCID 67431240, compound

Participants

Reaction Steps

To a stirred solution of PPh3 (300 mg, 1.14 mmol) in dry CH2Cl2 (7 mL) was added I2 (295 mg, 1.16 mmol) in one time. After 15 min, imidazole (90 mg, 1.32 mmol) was added. The mixture was stirred at room temperature for 20 min, and then 5-(6-hydroxy-1-hexanyl)-3-(1-methyl-2(S)-pyrrolidinylmethoxy)pyridine (150 mg, 0.52 mmol) in CH2Cl2 (1 mL) was added in dropwise. After stirred at room temperature for additional 3 h, the reaction mixture was quenched by addition of brine and diluted with CH2Cl2 (50 mL). The organic phase was separated, washed with aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated. The residue was purified by chromatography with EtOAc-Et3N (1:0 to 25:1) to give an oil (190 mg, 92%). 1H NMR (CDCl3) δ 8.23 (s, 2H), 7.19 (s, 1H), 3.99 (dd, 1H, J=9.3, 5.4 Hz), 3.92 (dd, 1H, J=9.3, 5.4 Hz), 3.25 (t, 2H, J=6.8 Hz), 3.14-3.08 (m, 1H), 2.69-2.61 (m, 1H), 2.48 (s, 3H), 2.46 (t, 2H, J=6.6 Hz), 2.35-2.26 (m, 1H), 2.10-1.95 (m, 1H), 1.90-1.65 (m, 5H); 13C NMR (CDCl3) δ 154.41, 144.55, 137.10, 123.04, 120.82, 92.51, 77.83, 71.15, 63.97, 57.65, 41.65, 32.33, 29.09, 28.48, 22.99, 18.35, 5.97.

Provenance & Evidence