HCID 58229494, compound → HCID 58229504, compound

Participants

Reaction Steps

To a solution of N-(2-chloro-5-(4-(3,6-dihydro-2H-pyran-4-yl)quinolin-6-yl)pyridin-3-yl)methanesulfonamide (0.055 g, 0.13 mmol) in (10 mL) under N2 was added platinum (IV) oxide (0.015 g, 0.066 mmol). The reaction mixture was purged with N2 followed by evacuating. This procedure was done 3 times. After last evacuation, a hydrogen balloon was inserted. The reaction was stirred at rt under H2 for 4 h. The reaction mixture was passed through a pad of Celite® (diatomaceous earth). The reaction mixture was then concentrated. The crude product was purified by column chromatography (12 g, 20% to 30% acetone in hexanes) to afford the desired product as an off-white solid (30.0 mg). MS (ESI pos. ion) m/z: calcd for C20H26ClN3O3S: 417.1; found: 417.9 [M+1]. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.85-2.14 (m, 4 H) 3.14 (s, 3 H) 3.55-3.85 (m, 3 H) 4.10-4.29 (m, 2 H) 6.93 (br. s., 1 H) 7.39 (d, J=4.53 Hz, 1 H) 7.92 (dd, J=8.70, 1.97 Hz, 1 H) 8.17-8.37 (m, 3 H) 8.57 (d, J=2.34 Hz, 1 H) 8.94 (d, J=4.53 Hz, 1 H).

Provenance & Evidence