Water → HCID 178419487, compound

Participants

Reaction Steps

To a solution of 7-phenyl-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline (0.018 g, 0.060 mmol) in dichloromethane (2 mL) was added N-bromosuccinimide (0.011 g, 0.063 mmol). The reaction was stirred at room temperature for 16 hours followed by addition of water (2 mL) and dichloromethane (3 mL). The organic layer was separated, dried using Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified using flash column chromatography (SiO2, 10% EtOAc in hexane) to give the pure desired product, 1-bromo-7-phenyl-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline as a yellow solid (0.010 g, 44%). M.p.=176-178° C.; 1H NMR (DMSO-d6, 400 MHz) δ 9.36 (m, 1H), 8.63 (s, 1H), 8.49 (s, 1H), 7.56 (m, 2H), 7.30-7.15 (m, 6H), 4.73 (t, J=7.2 Hz, 1H), 3.42 (m, 2H); LCMS [M+H]: 377; Elemental analysis (%): C, 63.59; H, 4.10; N, 10.98. Calcd for C20H14BrN3: C, 63.85; H, 3.75; N, 11.17.

Provenance & Evidence