Nitrogen → 6-(o-Tolyl)-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 (˜1 mol %), and Cs2CO3 (17.8 mg, 0.0547 mmol) in DME/H2O/EtOH (7/3/2, 0.5 mL). O-tolyl boronic acid (6.3 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 6 mg (23%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 451 (M−H)+; 1H NMR (300 MHz, DMSO) δ ppm 1.78-1.86 (m, 2H), 2.19 (br d, 2H), 2.22 (s, 3H), 3.13-3.19 (m, 2H), 3.58 (br d, 2H), 3.81-3.92 (m, 3H), 5.43 (s, 1H), 6.34-6.40 (m, 1H), 6.88 (d, 1H), 7.23-7.43 (m. 10H), 7.54 (m, 2H), 8.14 (d, 1H).

Provenance & Evidence