Phenyl isocyanate → HCID 178521947, compound

Participants

Reaction Steps

To a solution of 1-bromo-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium chloride (0.16 g, 0.55 mmol) in dichloromethane (5 mL), Hunig's Base (0.59 mL, 3.3 mmol) was added and stirred under inert atmosphere. After 10 minutes, phenyl isocyanate (0.06 mL, 0.57 mmol) was added and the reaction was allowed to stir at room temperature for 2 hours. The mixture was diluted with dichloromethane (10 mL) and washed with water (2×5 mL), dried over anhydrous sodium sulfate, filtered and dried in vacuo. The resulting pale brown solid was purified by flash column chromatography (SiO2, 50% ethyl acetate in hexanes) to give the desired product as light pink solid (0.6 g, 30%). M.p.=249-250° C., 400 MHz 1H NMR (DMSO-d6) δ: 10.64 (s, 1H), 9.66 (s, 1H), 8.82 (s, 1H), 8.25 (s, 1H), 7.90 (d, J=7.6 Hz, 1H), 7.68 (d, J=8.8 Hz, 2H), 7.2 (d, J=8.8 Hz, 2H), 7.07 (t, J=7.2 Hz, 1H), 6.95 (d, J=6.4 Hz, 1H), 4.25 (t, J=5.2 Hz, 2H), 3.24 (s, 2H), 2.96 (t, J=6 Hz, 2H), 2.2-2.14 (m, 2H); LCMS [M+H]: 350.

Provenance & Evidence