Nitrogen → N-(5-ethenyl-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-(5-bromo-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine D24 (1.8 g, 0.0047 mol) and vinyl tri(n-butyl)tin (1.58 mL, 0.0054 mol) in toluene (70 mL) was added, under a positive flow of N2, triphenyl phosphine (0.295 g, 1.125 mmol) and bis(dibenzylidene acetone)palladium (0) (0.338 g, 0.675 mmol). The mixture was put under a N2 atmosphere and heated at 130° C. for 1.5 hours (LC/MS was used to monitor the reaction). After the reaction was completed the reaction mixture was cooled to room temperature, filtered through a celite pad, and washed with dichloromethane. The filtrate was washed with 10% of aqueous NH4OH solution (3×50 mL), H2O (3×50 mL), and dried with Na2SO4, and concentrated in vacuo. The resulting residue was redissolved in acetonitrile. 416 mg of the title compound was crystallized out and the resulted solution was purified by using a Gilson preparative HPLC system with a Waters Xterra (C-18) column 100 mm by 50 mm ID, eluting with 10% B to 90% B in 10 min, where A=H2O and B=CH3CN pumped at 150 mL/min to yield additional 578 mg of the title compound (overall 994 mg, 67% yield). MS (ESI): 332 [M+H]+; 1H NMR (400 MHz, CDCl3): δ 1.67 (6H, m), 2.11 (2H, d), 2.47 (3H, m), 2.90 (2H, m), 3.39 (2H, t), 3.61 (1H, m), 4.03 (2H, dd), 5.47 (1H, d), 5.88 (1H, d), 6.66 (1H, dd), 6.75 (2H, m), 8.14 (1H, d), 8.23 (1H, d).

Provenance & Evidence