Nitrogen → 6-Phenyl-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One

Participants

Reaction Conditions

Reaction Steps

Into a dry microwave vial under N2 was added 6-bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(PPh3)Cl2 (about 1 mol %), and Cs2CO3 (17.8 mg, 0.0547 mmol) in DME/H2O/EtOH (7/3/2, 0.5 mL). Phenyl boronic acid (5.6 mg, 0.046 mmol) was added and the solution was heated in the microwave for 5 minutes at 160° C., filtered, and was purified by Prep HPLC to give 5.86 mg (23%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 435 (M−H)+; 1H NMR (300 MHz, DMSO) δ ppm 1.83-1.91 (m, 2H), 2.24 (br d, 2H), 3.15-3.23 (m, 2H), 3.61 (br d, 2H), 3.82-3.97 (m, 3H), 5.45 (s, 1H), 6.36-6.42 (m, 1H), 6.90 (d, 1H), 7.34-7.56 (m. 10H), 7.74 (d, 2H), 7.89 (dd, 1H), 8.40 (d, 1H).

Provenance & Evidence