A vial was charged with 5-bromo-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (51.89 mg, 0.100 mmol), Xantphos (11.56 mg, 0.020 mmol), Pd2(dba)3 (9.15 mg, 9.99 μmol), and cesium carbonate (65.1 mg, 0.200 mmol). The vial was flushed with Ar (g), then toluene (999 μl) and 2-phenylpyrrolidine (19.12 μl, 0.130 mmol) were added in sequence. The vial was sealed and heated to 100° C. for 18 h. The mixture was partitioned between EtOAc and water. The layers were separated, and the organic extract was washed with brine. The combined aq. layers were extracted with EtOAc, and the organic layers were combined. The combined solution was dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (0 to 50% EtOAc/Heptane) to give a clear oil. This oil was taken up in DCM (1 mL) and TFA (0.5 mL). After 2 h, the mixture was diluted with MeOH, then concentrated. The residue was taken up in diethyl ether, sonicated, then filtered. The collected solid was washed with diethyl ether (twice), dried under a stream of N2 (g) for 10 min, then dried under a high vacuum to give 5-(2-phenylpyrrolidin-1-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (15.25 mg, 0.035 mmol) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=12.76 (br. s., 1H), 8.45 (d, J=9.0 Hz, 1H), 8.31 (d, J=1.7 Hz, 1H), 7.77 (dd, J=2.0, 8.9 Hz, 1H), 7.59 (d, J=8.1 Hz, 1H), 7.40 (d, J=7.1 Hz, 2H), 7.33 (t, J=7.9 Hz, 1H), 7.26 (d, J=4.6 Hz, 1H), 7.18 (t, J=7.5 Hz, 2H), 7.12-7.04 (m, 2H), 6.82 (d, J=4.6 Hz, 1H), 4.86-4.77 (m, 1H), 4.20-4.10 (m, 1H), 3.02 (dt, J=4.7, 8.9 Hz, 1H), 2.47-2.39 (m, 1H), 2.16-2.05 (m, 1H), 2.00-1.78 (m, 2H). m/z (ESI) 436.2 (M+H)+.
