4-Fluorophenyl isocyanate → 1-(3,4-Difluorophenyl)-N-(4-fluorophenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

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Reaction Steps

To a stirred solution of 1-(3,4-difluorophenyl)-1,2,3,4-tetrahydroisoquinoline (0.1019 g, 0.415 mmol) in 3 mL of DCM, 4-fluorophenyl isocyanate (0.0550 mL, 0.484 mmol) was added. The clear solution was stirred for 1 h. The solvent was evaporated and residue was taken into small amount of DCM. The resulting precipitate was collected to yield the title compound as a white solid. The filtrate was concentrated and purified by silica gel chromatography (0-30% EtOAc in hexanes) to afford another batch of the title compound as a white solid. MS (ESI pos. ion) m/z: 383 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.16-7.37 (m, 6H) 6.93-7.13 (m, 5H) 6.54 (s, 1H) 6.40 (s, 1H) 3.66 (t, J=6.28 Hz, 2H) 2.77-3.08 (m, 2H).

Provenance & Evidence