Iodine → 2-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}-1,3,4-oxadiazole

Participants

Reaction Steps

Triphenylphosphine (0.203 g, 0.78 mmol), iodine (0.198 g, 0.78 mmol) and triethylamine (0.217 mL, 1.56 mmol) were dissolved in dichloromethane (5 mL). The mixture was stirred at room temperature for 10 minutes. N′-formyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbohydrazide (0.145 g, 0.39 mmol) in dichloromethane (5 mL) was added. The mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (100 mL) and washed with water (25 mL). The organic was dried over sodium sulphate, filtered and concentrated in vacuo to provide a yellow oil. This was purified using preparative HPLC on Fraction-Lynx® eluting with water:acetonitrile:trifluoroacetic acid (95:5:0.1) to provide the title compound (0.028 g, 20%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ1.78-1.85 (m, 4H), 2.05 (m, 2H), 2.30 (m, 2H), 2.56-2.60 (m, 4H), 2.60-2.70 (m, 4H), 3.59 (m, 2H), 3.90-4.05 (m, 4H), 6.90 (d, 2H), 7.20 (d, 2H), 8.30 (s, 1H). HRMS ESI+ m/z 358.2117 [MH]+.

Provenance & Evidence